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

HRID 17442
Notes
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Reaction equation

HRID 17442 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[O:4][C:5]2[C:6](=[C:8]([C:20]#[N:21])[C:9]([CH3:19])=[C:10]([C:13]3[N:14]=[C:15]([CH3:18])[S:16][CH:17]=3)[C:11]=2F)[N:7]=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>CS(C)=O.C(OCC)(=O)C>[CH3:1][N:2]([CH3:22])[C:3]1[O:4][C:5]2[C:6](=[C:8]([C:20]#[N:21])[C:9]([CH3:19])=[C:10]([C:13]3[N:14]=[C:15]([CH3:18])[S:16][CH:17]=3)[C:11]=2[N:34]2[CH2:35][CH2:36][C@H:32]([N:31]([CH3:37])[CH3:30])[CH2:33]2)[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685853432-(Dimethylamino)-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685857222-(dimethylamino)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

2-(Dimethylamino)-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile (I-171) (0.44 g, 1.39 mmol) was suspended in dimethyl sulfoxide (10 ml), then triethylamine (0.42 ml 3.03 mmol) and (3S)-3-(dimethylamino)pyrrolidine (0.38 ml, 3.00 mmol) were added, followed by stirring at an external temperature of about 110° C. for 4 hours. This was diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=50:1 to 10:1) to obtain a brown amorphous substance (0.51 g, 83%).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=50:1 to 10:1)
  5. customto obtain a brown amorphous substance (0.51 g, 83%)

Sources & evidence

ORD record
ord-fb891ccb48cb47bb8e581d1314cd2516
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