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Water → 2-cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17339
Notes
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Reaction equation

HRID 17339 reaction equation
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:21]#[N:22])[C:10]([CH3:20])=[C:11]([C:14]4[N:15]=[C:16]([CH3:19])[S:17][CH:18]=4)[C:12]=3F)[N:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:30][N:31]([CH3:37])[C@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1.O>CS(C)=O>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:21]#[N:22])[C:10]([CH3:20])=[C:11]([C:14]4[N:15]=[C:16]([CH3:19])[S:17][CH:18]=4)[C:12]=3[N:34]3[CH2:35][CH2:36][C@H:32]([N:31]([CH3:37])[CH3:30])[CH2:33]3)[N:8]=2)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685848052-Cyclopropyl-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685851302-cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile
Yield 61.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

2-Cyclopropyl-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile (I-80) (3.96 g, 12.65 mmol) was dissolved in dimethyl sulfoxide (40 ml), then triethylamine (4.27 ml, 30.36 mmol) and (3S)-3-(dimethylamino)pyrrolidine (1.93 ml, 15.18 mmol) were added, followed by stirring at 90° C. for 4 hours under nitrogen atmosphere. After cooling to room temperature, water was added, the precipitated solid was collected by filtration, recrystallized and purified with a mixed solvent of diethyl ether/ethyl acetate/methanol to obtain the entitled compound (3.16 g, 61%) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. customrecrystallized
  4. custompurified with a mixed solvent of diethyl ether/ethyl acetate/methanol

Sources & evidence

ORD record
ord-1395720e778f40bfa43487fd4afb8df8
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes