Structure of 78473-00-4
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CAS No. : | 78473-00-4 |
Formula : | C7H4Cl2N2 |
M.W : | 187.03 |
SMILES Code : | C1=C(C(=C(C=C1C#N)Cl)N)Cl |
MDL No. : | MFCD00017341 |
InChI Key : | COFNCCWGWXFACE-UHFFFAOYSA-N |
Pubchem ID : | 522706 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H317 |
Precautionary Statements: | P280 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 45.58 |
TPSA ? Topological Polar Surface Area: Calculated from |
49.81 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.7 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.78 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.46 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.97 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.37 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.26 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.15 |
Solubility | 0.131 mg/ml ; 0.0007 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.48 |
Solubility | 0.0616 mg/ml ; 0.00033 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.36 |
Solubility | 0.082 mg/ml ; 0.000439 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.47 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.59 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In N,N-dimethyl-formamide; 1,2-dichloro-benzene; at 160℃; for 0.166667h; | Intermediate 13: 3,5-Dichloro-4-isothiocyanato-benzonitrile To a solution of <strong>[78473-00-4]4-amino-3,5-dichloro-benzonitrile</strong> (2.1 g, 11 mmol) and DMF (0.3 mL, 3.2 mmol) in 1,2-dichlorobenzene (15 mL) was added thiophosgene (2.6 g, 23 mmol). The resulting solution was heated to 160 C. and held at that temperature for 10 min then cooled to rt. The room temperature solution was purified by a plug of silica (220 g) using 10% EtOAc-hexanes (750 mL) to afford the title compound as a colorless solid (2.4 g, 95%). MS (ESI): mass calcd. for C8H2Cl2N2S, 227.9; m/z found, 229.0 [M+H]+. 1H NMR (CDCl3): delta 7.63 (s, 2H). 13C NMR (CDCl3): 6143.7, 133.5, 133.6, 131.5, 115.8, 111.0. |
75% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 5h; | 3,5-Dichloro-4-isothiocyanatobenzonitrile To a cooled (0 C.) solution of <strong>[78473-00-4]4-amino-3,5-dichlorobenzonitrile</strong> (1 equiv.) in anhydrous DCM (0.5 M) was added DIEA (3 equiv.) in one portion. SCCl2 (3 equiv.) was added dropwise over 20 min. After the addition, the reaction mixture was stirred for about 5 h at 0 C. The solvent was evaporated to give a brown solid, which was purified by column chromatography on silica gel (petroleum/ethyl acetate=25/1) to give 3,5-dichloro-4-isothiocyanatobenzonitrile as a light yellow solid (75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine;palladium/carbon catalyst; In hydrogenchloride; methanol; dichloromethane; acetonitrile; | EXAMPLE 35 Synthesis of 1-(4-t-butylbenzyl)-3-(3,5-dichloro-4-methanesulfonylaminobenzyl)thiourea (5-7) 4-Amino-3,5-dichlorobenzonitrile (1 g) was dissolved in acetonitrile (50 ml) and to the solution were added triethylamine (890 mul) and methanesulfonyl chloride (670 mg), followed by refluxing for 8 hours. The mixture was extracted with water and dichloromethane, dried, concentrated, and then purified by column-chromatography (hexane/ethyl acetate=4/1) to obtain a compound (80 mg) as a liquid. The obtained compound was dissolved in methanol (10 ml), and then the solution was stirred for 15 hours in the presence of a small amount of concentrated hydrochloric acid and 5% palladium/carbon catalyst to hydrogenate the compound. The reaction solution was filtered through celite and concentrated. The concentrate was dissolved in dichloromethane (5 ml) and to the solution were added 4-t-butylbenzylisothiocyanate (54 mg) and triethylamiine (500 mul), followed by stirring at room temperature for 15 hours. The resulting mixture was extracted with water and dichloromethane, and then purified by column-chromatography (hexane/ethyl acetate=2/1) to yield the compound 5-7 (38 mg) as a liquid. 1H NMR(300 MHz, CDCl3): delta 7.42-7.23(r, 6H), 6.23(brs, 1H), 5.87(brs, 11), 4.85-4.82(ni, 211), 4.58-4.56(m, 2H), 3.57(s, 3H), 1.31(s,9H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; sulfuryl dichloride; In chloroform; | EXAMPLE 15 (+-)-(2E,4E) N-(1,2-Dimethylpropyl)-5-[trans-2-(3,5-dichloro-4-bromophenyl)cyclopropyl]penta-2,4-dienamide (compound 61) P-Aminobenzonitrile (11.8 g) (ex Aldrich) in dry chloroform (250 ml) under nitrogen was treated with sulphuryl chloride (4.05 g) (ex BDH) maintaining reaction temperature below 35. After 2 hours at reflux the mixture was poured onto ice and made alkaline with 2M sodium hydroxide solution. Work up in the usual manner gave 3,5-dichloro-4-aminobenzonitrile (18.2 g) NMR 1 H 7.35(2H,s), 4.70(2H,bs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen bromide; sodium nitrite; In concentrated hydrobromic acid; water; | The above aminonitrile (18.7 g) in concentrated hydrobromic acid (190 ml) at 0 was treated with sodium nitrite (7.6 g) in water (30ml). The resulting mixture was poured onto cuprous bromide (28.7 g) in water (180 ml) and hydrobromic acid (30 ml) at 50. After 2 hours at 50 and 18 hours at 25 the mixture was diluted with water and worked up in the usual manner to give 3,5-dichloro-4-bromobenzonitrile (9.2 g). NMR 1 H: 7.63(2H,s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 3 3,5-Dichloro-4-amino benzylnitrile The product from Example 2 (125 g) was dissolved in ether (300 mL) and added with stirring to an ice cooled mixture of concentrated HCl (300 mL) and ether (200 mL). A solid resulted which was filtered after 15 minutes and added to an ice cold suspension of powdered NaCN (86 g) in DMSO (430 mL). The mixture was heated to 60 C. and stirred for 45 minutes. The reaction was cooled, ice added, and the solid filtered. The filtered solid was dissolved in CH2 Cl2 (400 mL), then washed successively with dilute aqueous NaOH and then saturated brine. The organic layer was separated and dried (MgSO4) to afford 67 g of the desired product, mp 117-119 C. | ||
As examples of relevant diazo compounds the following amines may be mentioned: ... 1-amino-2-methylsulphonyl-4-nitrobenzene, 1-amino-2,4-dinitrobenzene, 1-amino-2,4-dicyanobenzene, 1-amino-2-cyano-4-methylsulphonylbenzene, 1-amino-2,6-dichloro-4-cyanobenzene, 1-amino-2,6-dichloro-4-nitrobenzene, 1-amino-2,4-dicyano-6-chlorobenzene, 1-amino-2,4,6-trinitrobenzene, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; ethylenediamine; In methanol; 1,2-dimethoxyethane; HCl (g); ethanol; chloroform; acetonitrile; | EXAMPLE 4 2-[(3,5-Dichloro-4-aminobenzyl)]imidazoline hydrochloride The product of Example 3 (10 g) was dissolved in DME (80 mL) and MeOH (9.5 mL). The solution was cooled in an ice bath and HCl (g) was bubbled through the solution for 30 minutes. The reaction flask was stoppered and allowed to stand at room temperature overnight. The solution was concentrated, ether (50 mL) was added, and the resulting solid was filtered. The solid was added to EtOH (80 mL) and the solution was cooled, followed by addition of ethylenediamine (17.8 mL). After stirring for 15 minutes, the solution was refluxed for 15 minutes. The reaction mixture was concentrated and CHCl3 (40 mL) was added, followed by addition of H2 O and aqueous 45% KOH (5 mL). After mixing, the organic layer was separated and washed with H2 O (2*50 mL). The organic layer was again separated and methanolic HCl was added. After drying over MgSO4, evaporation provided a crude product. This was dissolved in CH3 CN (150 mL) and heated on a steam bath for about 3 minutes. The solution was cooled and the resulting crystals were filtered, washed with cold CH3 CN (20 mL) and then ether (20 mL), giving the desired product, mp 261-264 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With trifluoroacetic anhydride; In dichloromethane; | (i) Preparation of N-trifluoroacetyl-<strong>[78473-00-4]4-cyano-2,6-dichloroaniline</strong> Twenty-five grams (0.1337 mole) of <strong>[78473-00-4]4-cyano-2,6-dichloroaniline</strong> was dissolved in 250 ml of methylene chloride, and 30.9 g (20.8 ml, 0.1471 mole) of trifluoroacetic anhydride was added slowly with stirring. The solution was allowed to stand overnight and then was neutralized by the addition of 5% aqueous sodium carbonate, precipitating a white crystalline solid which was filtered and dried to give 28.0 g (74% yield) of N-trifluoroacetyl-<strong>[78473-00-4]4-cyano-2,6-dichloroaniline</strong>, m.p.: 134-136 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; | 1. Preparation of 4-cyano-2,6-dichlorobenzamine. Reaction of 4-cyanobenzamine (10 g., 0.085 m, Aldrich Chem. Co.) with 292 ml of 6N HCl and 30% H2 O2 (17.2 mL, 0.17 m) led to the formation of a white crystalline compound with a melting point of 113-115 C. The yield of this compound was 12.3 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; dihydrogen peroxide; In ethanol; water; | EXAMPLE V 3,5-Dichloro-4-(2-imidazolidinylideneamino)-benzenecarboxamide 3,5-Dichloro-4-(2-imidazolidinylideneamino)-benzenecarboxamide which structurally is STR10 may be made by the following procedures. Into a three-necked 500 mL round-bottomed flask equipped with a mechanical stirrer, reflux condenser, and thermometer and charged with 4-cyano-2,6-dichlorobenzamine (4 g., 0.016 m) in 30 mL of absolute ethanol is added hydrogen peroxide (9 mL of 30% in 81 mL of water) and potassium hydroxide (4.52 g. of 30% solution). The reaction mixture is heated to a temperature of 45 C. over a thirty-minute period and maintained at this temperature for two additional hours. At this time, the solution is cooled to 0 C. with an ice bath and filtered to yield 1.8 g. of whitish crystalline material. Subsequent reduction in volume of the filtrate results in an additonal 1.1 g. of the same material coming out of solution for a crude yield of 2.9 g. or 68% of theoretical. Recrystallization from water/ethanol solvent leads to a light yellow powder which has a melting point of 243-245 C. and gives the expected IR with double absorption in the 1700 to 1640 cm-1 region. Elemental analysis for the salt shows it has the following composition: calculated for C10 H10 N4 Cl2: C 43.98%, H 3.69%, N 20.51%, Cl 25.96%; observed: C 43.82%, H 3.79%, N 20.39%, Cl 26.08%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; ethyl acetate; | EXAMPLE 17 2-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (2,6-dichloro-4-cyanophenyl)amide Starting from 2-ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.10 g) and <strong>[78473-00-4]4-amino-3,5-dichlorobenzonitrile</strong> (0.12 g). Purification by column chromatography on silica with 20% then 30% then 50% ethyl acetate in hexane to give the title compound (0.051 g) as a cream solid. TLC Rf 0.125 (20% ethyl acetate in hexane) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | EXAMPLE 21 7-Difluoromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid (2,6-dichloro-4-cyanophenyl)amide Starting from 7-difluromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (100 mg) and <strong>[78473-00-4]4-amino-3,5-dichlorobenzonitrile</strong> (99 mg). Purification by column chromatography on silica eluding with 1% methanol in dichloromethane afforded the title compound as a white solid (12 mg). TLC Rf 0.65 (2.5% methanol in dichloromethane) m.p. 208-210 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | To lithium aluminum hydride (0.57 g, 15 mmol) in dry THF (20 mL) was added dropwise <strong>[78473-00-4]3,5-dichloro-4-aminobenzonitrile</strong> (1.87 g, 10 mmol) in THF (30 mL). The mixture was stirred at RT for 2 hours. Then, sodium sulfate decahydrate (4.83 g, 15 mmol) was added and stirred for 30 min. The solid was filtered off and washed with THF for three times. The solvent was removed by rotovap and residue was purified by column with Methanol/DCM (3:7) as the eluant. 3,5-Dichloro-4-aminobenzylamine was obtained as an off-white solid (1.5 g, 80%). 1H NMR (300 MHz, CD3OD): delta 3.65 (s, 2H), 7.2 (s, 2H). | |
80% | Preparation A; 3,5-Dichloro-4-aminobenzylamine; Step A (1); To lithium aluminum hydride (0.57 g, 15 mmol) in dry THF (20 mL) was added dropwise <strong>[78473-00-4]3,5-dichloro-4-aminobenzonitrile</strong> (1.87 g, 10 mmol) in THF (30 mL). The mixture was stirred at rt for 2 h. Then, sodium sulfate decahydrate (4.83 g, 15 mmol) was added and the mixture was stirred for 30 min. The solid was filtered off and washed with THF three times. The solvent was removed under vacuum and the residue was purified by chromatography with Methanol/DCM (3:7) as the eluant. 3,5-Dichloro-4-aminobenzylamine was obtained as an off-white solid (1.5 g, 80%). 1H NMR (300 MHz, CD3OD): delta3.65 (s, 2H), 7.2 (s, 2H). | |
80% | Preparation B 3,5-Dichloro-4-aminobenzylamine To lithium aluminum hydride (0.57 g, 15 mmol) in dry THF (20 mL) was added dropwise <strong>[78473-00-4]3,5-dichloro-4-aminobenzonitrile</strong> (1.87 g, 10 mmol) in THF (30 mL). The mixture was stirred at RT for 2 hours. Then, sodium sulfate decahydrate (4.83 g, 15 mmol) was added and stirred for 30 min. The solid was filtered off and washed with THF for three times. The solvent was removed by rotovap and residue was purified by column with Methanol/DCM (3:7) as the eluant. 3,5-dichloro-4-aminobenzylamine was obtained as an off-white solid (1.5 g, 80%). 1H NMR (300 MHz, CD3OD): delta 7.2 (s, 2 H), 3.65 (s, 2 H). |
80% | 3,5-Dichloro-4-aminobenzylamine To lithium aluminum hydride (0.57 g, 15 mmol) in dry THF (20 mL) was added dropwise <strong>[78473-00-4]3,5-dichloro-4-aminobenzonitrile</strong> (1.87 g, 10 mmol) in THF (30 mL). The mixture was stirred at rt for 2 h. Then, sodium sulfate decahydrate (4.83 g, 15 mmol) was added and the mixture was stirred for 30 min. The solid was filtered off and washed with THF three times. The solvent was removed under vacuum and the residue was purified by chromatography with Methanol/DCM (3:7) as the eluant. 3,5-Dichloro-4-aminobenzylamine was obtained as an off-white solid (1.5 g, 80%). 1H NMR (300 MHz, CD3OD): delta3.65 (s, 2H), 7.2 (s, 2H). | |
80% | To lithium aluminum hydride (0.57 g, 15 mmol) in dry THF (20 mL) was added dropwise <strong>[78473-00-4]3,5-dichloro-4-aminobenzonitrile</strong> (1.87 g, 10 mmol) in THF (30 mL). The mixture was stirred at rt for 2 h. Then, sodium sulfate decahydrate (4.83 g, 15 mmol) was added and the mixture was stirred for 30 min. The solid was filtered off and washed with THF three times. The solvent was removed under vacuum and the residue was purified by chromatography with Methanol/DCM (3:7) as the eluant. 3,5-Dichloro-4-aminobenzylamine was obtained as an off-white solid (1.5 g, 80%). 1H NMR (300 MHz, CD3OD): delta 3.65 (s, 2H), 7.2 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of <strong>[78473-00-4]4-amino-3,5-dichlorobenzonitrile</strong> (2.00 g, 10.63 mmol) in acetonitrile (12 ml) was added dropwise tetrafluoroboric acid (2.80 ml, 21.27 mmol). After stirring for 10 min, isoamyl nitrite (1.50 ml, 10.63 mmol) was added and the reaction mixture was cooled to 0 C. After a further 10 min, diethyl ether (50 ml) was added and the resulting precipitate was collected by filtration and dried to give the titled compound (1.9 g). 1H-NMR (D2O): 8.36-8.40 (2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step B (1): To a solution of 3,5-dichloro-4-amino-benzonitrile (187 mg, 1 mmol) in 4 mL of THF at room temperature was added 2.2 mL of 1.0 M NaHMDS in THF. The resulting reaction mixture was stirred at room temperature for 30 min, at which time acetyl chloride (3.1 mmol) was added. DCM (100 mL) and water (100 mL) were added to the reaction mixture after being stirred overnight, followed by the addition of 5 mL of a 1.4 N HCl aqueous solution. The layers were separated and the aqueous layer was extracted with DCM (2*100 mL). The extracts were combined and solvents were evaporated in vacuo. The residue was purified by HPLC to give 4-acetamido-3,5-dichloro-benzonitrile. MS (ESI) (M-H)+=227.05. 1H-NMR (300 MHz, CDCl3) delta 7.63 (s, 2H), 2.21 (s, 3H). | ||
To a solution of 3,5-dichloro-4-amino-benzonitrile (187 mg, 1 mmol) in 4 mL of THF at room temperature was added 2.2 mL of 1.0 M NaHMDS in THF. The resulting reaction mixture was stirred at room temperature for 30 min, at which time acetyl chloride (3.1 mmol) was added. DCM (100 mL) and water (100 mL) were added to the reaction mixture after being stirred overnight, followed by the addition of 5 mL of a 1.4 N HCl aqueous solution. The layers were separated and the aqueous layer was extracted with DCM (2*100 mL). The extracts were combined and solvents were evaporated in vacuo. The residue was purified by HPLC to give 4-acetamido-3,5-dichloro-benzonitrile. MS (ESI) (M-H)+=227.05. 1H NMR (300 MHz, CDCl3) delta 7.63 (s, 2H), 2.21 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With titanium tetrachloride; triethylamine; In dichloromethane; at 0 - 20℃; for 1h;Reduced presure; | Step 3 :4-[l-(4-Azido-5-chloropyridin-3-yl)meth-(E)-ylidene]amino}-3,5-dichlorobenzonitrile To a cooled (0 C) solution of 4-azido-5-chloropyridine-3-carbaldehyde (2.0 g, 10.95 mmol), 4-amino-3,5- dichlorobenzonitrile (2.05 g, 10.95 mmol) and triethylamine (4.6 mL, 6.57 mmol) in DCM (48 mL) was added titanium tetrachloride (1M in DCM, 6.6 mL, 6.57 mmol) drop wise over 10 minutes. The reaction mixture was stirred for 20 minutes, warmed to room temperature, and stirred for an additional 30 minutes. The resultant mixture was concentrated to dryness under reduced pressure to afford the title compound which was used without further purific |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With titanium tetrachloride; triethylamine; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere; | Method 2: Example 19: 3^-Dichloro-4-[4-(2,6-dimethylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitri Step 1 : 4-[l-(4-Azidopyridin-3-yl)meth-(E)-ylidene]amino}-3,5-dichlorobenzonitrile Triethylamine (8.9 mL, 64.2 mmol) was added to a cooled (0 C) mixture of 4-azidopyridine-3-carbaldehyde (3.2 g, 21.4 mmol) and <strong>[78473-00-4]4-amino-3,5-dichlorobenzonitrile</strong> (4.0 g, 21.4 mmol) in DCM (80 mL) under nitrogen. Titanium tetrachloride (1M, 12.8 mL, 12.8 mmol) was added and then the reaction mixture was stirred for 1 hour at 0 C. After warming to room temperature, the reaction was stirred for an additional 2 h and then concentrated under reduced pressure. The residue was suspended in toluene and filtered though a pad of Celite. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as an orange solid. This crude material was employed in the next step without further purification or analysis. |
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