146074-43-3|(R)-Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride| Ambeed

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Quality Control of [ 146074-43-3 ] Purity: 95% SDS Specification

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Product Details of [ 146074-43-3 ]

CAS No. :	146074-43-3
Formula :	C₁₁H₁₄ClNO₂
M.W :	227.69
SMILES Code :	O=C([C@@H]1NCC2=C(C=CC=C2)C1)OC.[H]Cl
MDL No. :	MFCD07778614

Safety of [ 146074-43-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 146074-43-3 ]

* 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.

Downstream synthetic route of [ 146074-43-3 ]

[ 146074-43-3 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 41220-48-8 ]
[ 146074-43-3 ]

References: [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 1181 - 1187.

2
[ 1221440-30-7 ]
[ 146074-43-3 ]
C₂₁H₂₅NO₄ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 1181 - 1187.

3
[ 146074-43-3 ]
[ 138498-84-7 ]
C₂₁H₂₅NO₄ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 1181 - 1187.

4
[ 67-56-1 ]
[ 74163-81-8 ]
[ 146074-43-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With thionyl chloride; at 0 - 50℃;Inert atmosphere;	Example 93(3R)-2-(2-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-lH-pyrazol-l-yl)-5-(naphthalen-2- ylsulfonylcarbamoyl)benzoyl)- 1 ,2,3 ,4-tetrahydroisoquinoline-3 -carboxylic acid(93) Intermediate 93 A: (R)-Methyl l,2,3,4-tetrahydroisoquinoline-3-carboxylatehydrochloride[00326] To (5)-l,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Aldrich, 500 mg, 2.82 mmol) in MeOH (2.8 mL) was added SOCl2 (824 μ,, 11.3 mmol) at 0 C. The resulting reaction mixture was allowed to warm to room temperature over 5 h and then stirred at 50 C overnight. The reaction mixture was then concentrated in vacuo to give the title compound (457 mg, 71%) as a white solid. ¾ NMR (CDC13) δ 7.30-7.23 (m, 2H), 7.20-7.13 (m, 2H), 4.78-4.69 (m, 1H), 4.56-4.45 (m, 1H), 4.43-4.35 (m, 1H), 3.87 (s, 3H), 3.49-3.43 (m, 2H); MS(ESI+) m/z 192.1 (M+H)+.

References: [1]Patent: WO2012/162365,2012,A1 .Location in patent: Page/Page column 178-179.

5
[ 146074-43-3 ]
[ 1382257-14-8 ]
[ 1415095-26-9 ]

Yield	Reaction Conditions	Operation in experiment
37%		Intermediate 93 B: (3R)-Methyl 2-(2-(4-chloro-3-(dibutylcarbamoyl)-5 -methyl- 1H- pyrazol-l-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoyl)-l, 2,3,4- tetrahydroisoquinoline-3-carboxylate[00327] To 2-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-lH-pyrazol-l-yl)-5- (naphthalen-2-ylsulfonylcarbamoyl)benzoic acid (Intermediate 9 IF, 50 mg, 0.080 mmol) in CH2C12 (890 μ) was added l-chloro-N,N-2-trimethylprop-l -en- 1 -amine (21 μ., 0.16 mmol). After stirring for 30 min at room temperature, (R)-methyl 1,2,3,4- tetrahydroisoquinoline-3-carboxylate hydrochloride (20 mg, 0.088 mmol) in THF (900 μ,) was added followed by z'-Pr2EtN (42 μΕ, 0.24 mmol). The resulting reaction mixture was stirred at room temperature for 1 h, then quenched with sat. aq. NH4CI solution and extracted with EtOAc (1 x). The organic layer was washed with IN aq. HCl solution, and the combined aqueous layer was extracted with EtOAc (2 x). The combined organic extracts were dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (24 mg, 37%). lH NMR (1 : 1 CD30D:CDC13, 1 : 1 mixture of amide rotamers) δ 8.62 (d, J= 15.9 Hz, 1H), 8.20 (dd, J= 13.9, 9.0 Hz, 1.5H), 8.13-7.85 (m, 5H), 7.63-7.52 (m, 1.5H), 7.47 (d, J= 8.4 Hz, 1H), 7.24-7.06 (m, 3.5H), 6.93 (d, J= 6.8 Hz, 0.5 H), 5.17 (t, J= 5.4 Hz, 0.5H), 5.02 (d, J = 17.6 Hz, 0.5H), 4.75 (d, J= 5.9 Hz, 1H), 4.49 (d, J= 18.0 Hz, 1.5H), 3.64 (br s, 1.5H), 3.55-3.41 (m, 2.5H), 3.27-3.09 (m, 4H), 3.05-2.99 (m, 0.5H), 2.31 (s, 1.5H), 2.24 (s, 1.5H), 1.50-0.95 (m, 8H), 0.95-0.82 (m, 3H), 0.74 (t, J= 7.5 Hz, 1.5H), 0.71-0.63 (m, 1.5H); MS(ESI+) m/z 798.3 (M+H)+.

References: [1]Patent: WO2012/162365,2012,A1 .Location in patent: Page/Page column 179.

6
[ 912545-04-1 ]
[ 146074-43-3 ]
(R)-methyl 2-(2,4-bis(benzyloxy)-5-chlorobenzoyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 12h;	Compound 4 (2.213 g, 6 mmol) and compound 6 (1.639 g, 7.2 mmol)Dissolved in 30 mL of anhydrous dichloromethane,1-Hydroxybenzotriazole (HOBt, 0.973 g, 7.2 mmol)1- (3- dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI, 1.38 g, 7.2 mmol), N- methylmorpholine (NMM, 2.012 mL, 18 mmol)Stir at room temperature for 12 hours. The reaction solution was washed with water, 5% hydrochloric acid solution,Saturated NaHCO3, saturated brine, the organic phase was separated,Dried over anhydrous sodium sulfate, evaporated to dryness and the solvent was purified by silica gel column chromatography2.89 g Compound 7, yield: 81%.

References: [1]Patent: CN107311986,2017,A .Location in patent: Paragraph 0058; 0059.
[2]European Journal of Medicinal Chemistry,2018,vol. 143,p. 85 - 96.

7
[ 67-56-1 ]
[ 103733-65-9 ]
[ 146074-43-3 ]

Yield	Reaction Conditions	Operation in experiment
94.4%	With thionyl chloride; at 0 - 20℃; for 100h;	Compound 5 (4.27 g, 20 mmol) was added to 20 mL of methanol,After cooling to 0 C, 5.2 mL of thionyl chloride was added dropwise and the mixture was stirred at room temperature for 100 hours.Drying under reduced pressure, the residue was washed with ether,After drying, 4.3 g of light yellow solid compound 6 was obtained in a yield of 94.4%.
	With thionyl chloride; at 0℃; for 2h;Inert atmosphere; Reflux;	Thionyl chloride (210 μL, 3.12 mmol) was added dropwise to a solution of compound 10.1 (150 mg, 0.85 mmol) in methanol (5 mL) at 0 C. The reaction mixture was then refluxed for 2 h. The excess SOCl2 and methanol were then concentrated invacuo to get the crude compound 10.2 (132 mg). This compound was directly used in the next step without further purification.

References: [1]Patent: CN107311986,2017,A .Location in patent: Paragraph 0056; 0057.
[2]European Journal of Medicinal Chemistry,2018,vol. 143,p. 85 - 96.
[3]Bioorganic and Medicinal Chemistry,2021,vol. 29.

8
[ 146074-43-3 ]
(R)-2-(5-chloro-2,4-dihydroxybenzoyl)-N-(2-methoxybenzyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide [ No CAS ]