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[ CAS No. 89371-35-7 ] {[proInfo.proName]}

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2D 3D

Chemical Structure| 89371-35-7

Chemical Structure| 89371-35-7

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Quality Control of [ 89371-35-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89371-35-7 ]

SDS Specification

Alternatived Products of [ 89371-35-7 ]

Product Details of [ 89371-35-7 ]

CAS No. :	89371-35-7	MDL No. :	MFCD08689599
Formula :	C₁₂H₁₄N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	234.25	Pubchem ID :	-
Synonyms :

Safety of [ 89371-35-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89371-35-7 ]

* 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 [ 89371-35-7 ]

[ 89371-35-7 ] Synthesis Path-Downstream 1~11

1
[ 89371-35-7 ]
(S)-2-[(S)-1-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyl)-ethylamino]-decanoic acid ethyl ester [ No CAS ]
[ 89371-40-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate 1) THF, -50 deg C, 20 min, 2) THF, -30 deg C, 20 min; Yield given. Multistep reaction;

Reference： [1]Hayashi, Kimiaki; Nunami, Ken-ichi; Kato, Jyoji; Yoneda, Naoto; Kubo, Masami; et al. [Journal of Medicinal Chemistry, 1989, vol. 32, # 2, p. 289 - 297]

2
[ 89371-89-1 ]
[ 89371-35-7 ]

Yield	Reaction Conditions	Operation in experiment
83.3%	With hydrogen bromide; acetic acid for 0.333333h; Ambient temperature;

Reference： [1]Hayashi, Kimiaki; Nunami, Ken-ichi; Kato, Jyoji; Yoneda, Naoto; Kubo, Masami; et al. [Journal of Medicinal Chemistry, 1989, vol. 32, # 2, p. 289 - 297]

3
[ 89371-35-7 ]
[ 89371-41-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) tBuOK / 1) THF, -50 deg C, 20 min, 2) THF, -30 deg C, 20 min 2: H₂ / Pd / ethanol / 2 h / 760 Torr / Ambient temperature

Reference： [1]Hayashi, Kimiaki; Nunami, Ken-ichi; Kato, Jyoji; Yoneda, Naoto; Kubo, Masami; et al. [Journal of Medicinal Chemistry, 1989, vol. 32, # 2, p. 289 - 297]

4
[ 89384-29-2 ]
[ 89371-35-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 65.7 percent / K₂CO₃ / acetone / Ambient temperature 2: 83.3 percent / 25percent HBr-acetic acid / 0.33 h / Ambient temperature

Reference： [1]Hayashi, Kimiaki; Nunami, Ken-ichi; Kato, Jyoji; Yoneda, Naoto; Kubo, Masami; et al. [Journal of Medicinal Chemistry, 1989, vol. 32, # 2, p. 289 - 297]

5
[ 100-51-6 ]
[ 89371-35-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 85.2 percent / p-TosOH*H₂O / benzene / 16 h / Heating 2: 65.7 percent / K₂CO₃ / acetone / Ambient temperature 3: 83.3 percent / 25percent HBr-acetic acid / 0.33 h / Ambient temperature

Reference： [1]Hayashi, Kimiaki; Nunami, Ken-ichi; Kato, Jyoji; Yoneda, Naoto; Kubo, Masami; et al. [Journal of Medicinal Chemistry, 1989, vol. 32, # 2, p. 289 - 297]

6
aqueous sodium chloride [ No CAS ]
[ 65675-51-6 ]
[ 89371-35-7 ]
benzyl (4S)-1-methyl-3-[(2R)-2-(p-toluenesulfonyloxy)-propionyl]-2-oxoimidazolidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.8%	With thionyl chloride; acetic acid In tetrahydrofuran; chloroform; ethyl acetate	6.1 EXAMPLE 6 (1) To a solution of D-lactic acid O-tosylate (2g) in chloroform (20 ml) was added thionyl chloride (2.39 ml), and the mixture was heated under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, then reconcentrated with addition of chloroform to obtain an acid chloride (residue C). On the other hand, benzyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate (2.21 g) was dissolved in tetrahydrofuran (25 ml), and under cooling at -50° C., potassium t-butoxide (1.06 g) was added under nitrogen gas stream, followed by stirring for 20 minutes. To this solution was added at the same temperature a solution of the above acid chloride (residue C) in tetrahydrofuran (4 ml), followed by stirring for 20 minutes. To the reaction mixture were added a mixed solution of ethyl acetate (15 ml), acetic acid (0.57 g) and saturated aqueous sodium chloride (15 ml). The organic layer was taken by separation, successively washed with saturated aqueous sodium chloride, aqueous 5 % potassium carbonate, saturated aqueous sodium chloride, and then dried. Evaporation of the solvent and recrystallization of the residue from ethyl acetate gave benzyl (4S)-1-methyl-3-[(2R)-2-(p-toluenesulfonyloxy)-propionyl] -2-oxoimidazolidine-4-carboxylate (3.1 g). Yield: 82.8%, m.p.: 153°-155° C. [α]D25: +2.5° (C=2, chloroform). IRυmaxNujol (cm-1): 1740, 1730, 1695. NMR (CDCl3) δ: 1.48 (3H,d,J=7 Hz), 2.40 (3H,s), 2.82 (3H,s), 3.28 (1H,dd,J=4,10 Hz), 3.68 (1H,t,J=10 Hz), 4.66 (1H,dd,J=4,10 Hz), 5.10, 5.26 (1H*2,AB,J=12 Hz), 6.24(1H,q,J=7 Hz), 7.32 (5H,s), 7.25, 7.77 (2H each,A2 B2, J=8 Hz). MS m/z: 460 (M+)

Reference： [1]Current Patent Assignee: FORTUNE BRANDS HOME & SECURITY INC; MITSUBISHI CHEMICAL HOLDINGS CORPORATION - US5013845, 1991, A

7
[ 89371-35-7 ]
benzyl (4S)-1-methyl-3-[(2R)-2-(methanesulfonyloxy)propionyl]-2-oxoimidazolidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.8%		4.1 EXAMPLE 4 (1) D-lactic acid O-mesylate (1.97 g) and benzyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate (2.27 g) were treated similarly as in Example 1 - (1), and the crude product was purified by silica gel chromatography (ethyl acetate) and crystallized from isopropyl ether to give benzyl (4S)-1-methyl-3-[(2R)-2-(methanesulfonyloxy)propionyl]-2-oxoimidazolidine-4-carboxylate (3.01 g). Yield: 80.8%, m.p.: 98°-102° C. [α]D25: -5.0° (C=2, chloroform). IR υmaxNujol (cm-1); 1765, 1730, 1715, 1700. NMR (CDCl3) δ: 1.61 (3H,d,J=7 Hz), 2.86 (3H,s), 2.91 (3H,s), 3.36 (1H,dd,J=4,10 Hz), 3.73 (1H,t,J=10 Hz), 4.77 (1H,dd,J=4,10 Hz), 5.20 (2H,s), 6.35 (1H,q,J=7 Hz), 7.33 (5H,s). MS m/z: 384 (M+).

Reference： [1]Current Patent Assignee: FORTUNE BRANDS HOME & SECURITY INC; MITSUBISHI CHEMICAL HOLDINGS CORPORATION - US5013845, 1991, A

Yield	Reaction Conditions	Operation in experiment
83.3%		5.2 Preparation 5 (2) 10 g of benzyl (4S)-1-methyl-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate and 40 ml of a hydrogen bromide-acetic acid solution are treated in the same manner as described in Preparation 4-(3), whereby 5.3 g of benzyl (4S)-1-methyl-2-oxo-imidazolidine-4-carboxylate are obtained as colorless crystals. Yield: 83.3% M.p. 94°-95° C. IR νmaxnujol (cm-1): 3250, 1745, 1710, 1670 Mass (m/e): 234 (M+)

9
[ 89371-35-7 ]
(4S)-4-[[4-[2-[(2,6-dimethylpyrimidin-4-yl)amino]pyrazolo[1,5-a]pyridin-5-yl]-6-methyl-3-pyridyl]oxymethyl]-1-methylimidazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium tetrahydridoborate; calcium(II) chloride; ethanol / 12 h / 0 - 20 °C 2: N,N-dimethyl-4-aminopyridine / dichloromethane / 16 h / 20 °C 3: Cs₂CO₃ / N,N-dimethyl-formamide / 1 h / 110 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; MASS GENERAL BRIGHAM INC; BROAD INSTITUTE - WO2022/165529, 2022, A1

10
[ 89371-35-7 ]
(S)-4-(hydroxymethyl)-1-methylimidazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium tetrahydridoborate; ethanol; calcium(II) chloride at 0 - 20℃; for 12h;	365.A Example 365: (4S)-4-[[4-[2-[(2,6-dimethylpyrimidin-4-yl)amino]pyrazolo[1,5-a]pyridin-5-yl]- 6-methyl-3-pyridyl]oxymethyl]-1-methyl-imidazolidin-2-one. Step A. (S)-4-(hydroxymethyl)-1-methylimidazolidin-2-one. To a mixture of (S)-benzyl 1-methyl-2-oxoimidazolidine-4-carboxylate (340 mg, 1.45 mmol, 1 equiv.), CaCl2 (96.7 mg, 0.871 mmol, 0.6 equiv.) and EtOH (10 mL) at 0°C was added NaBH4 (66 mg, 1.7 mmol, 1.2 equiv.).The mixture was stirred at room temperature for 12 hr. The ethanol was removed under vacuum and the residue was dissolved in sat. aq. NH4Cl (5 mL). The mixture was extracted with EtOAc (20 mL x 3) and the product was detected in the aqueous phase. The aqueous phase was frozen using dry ice/ethanol, and then lyophilized to dryness to get the crude product. To the crude product was added MeOH (5 mL) and MeCN (100 mL) to remove salt. The mixture was filtered then concentrated to give the compound (S)-4-(hydroxymethyl)-1-methylimidazolidin-2- one as a colorless oil (160 mg, 85%)
85%	With sodium tetrahydridoborate; ethanol; calcium(II) chloride at 0 - 20℃; for 12h;	365.A Example 365: (4S)-4-[[4-[2-[(2,6-dimethylpyrimidin-4-yl)amino]pyrazolo[1,5-a]pyridin-5-yl]- 6-methyl-3-pyridyl]oxymethyl]-1-methyl-imidazolidin-2-one. Step A. (S)-4-(hydroxymethyl)-1-methylimidazolidin-2-one. To a mixture of (S)-benzyl 1-methyl-2-oxoimidazolidine-4-carboxylate (340 mg, 1.45 mmol, 1 equiv.), CaCl2 (96.7 mg, 0.871 mmol, 0.6 equiv.) and EtOH (10 mL) at 0°C was added NaBH4 (66 mg, 1.7 mmol, 1.2 equiv.).The mixture was stirred at room temperature for 12 hr. The ethanol was removed under vacuum and the residue was dissolved in sat. aq. NH4Cl (5 mL). The mixture was extracted with EtOAc (20 mL x 3) and the product was detected in the aqueous phase. The aqueous phase was frozen using dry ice/ethanol, and then lyophilized to dryness to get the crude product. To the crude product was added MeOH (5 mL) and MeCN (100 mL) to remove salt. The mixture was filtered then concentrated to give the compound (S)-4-(hydroxymethyl)-1-methylimidazolidin-2- one as a colorless oil (160 mg, 85%)

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; MASS GENERAL BRIGHAM INC; BROAD INSTITUTE - WO2022/165529, 2022, A1 Location in patent: Page/Page column 377
[2]Current Patent Assignee: JOHNSON & JOHNSON INC; MASS GENERAL BRIGHAM INC; BROAD INSTITUTE - WO2022/165529, 2022, A1 Location in patent: Page/Page column 377

11
[ 89371-35-7 ]
(S)-(1-methyl-2-oxoimidazolidin-4-yl)methyl 4-methylbenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium tetrahydridoborate; calcium(II) chloride; ethanol / 12 h / 0 - 20 °C 2: N,N-dimethyl-4-aminopyridine / dichloromethane / 16 h / 20 °C

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; MASS GENERAL BRIGHAM INC; BROAD INSTITUTE - WO2022/165529, 2022, A1

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P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P308 + P313	IF exposed or concerned: Get medical advice/attention.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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