Triethylamine → 4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

HRID 17371Notes

Reaction equation

HRID 17371 reaction equation
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[C:9]([C:11]1[C:16]2[N:17]=[C:18]([C:20]([NH:22][CH3:23])=[O:21])[O:19][C:15]=2[C:14](F)=[C:13]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]=1[CH3:31])#[N:10].C(N(CC)CC)C>CS(C)=O>[C:9]([C:11]1[C:16]2[N:17]=[C:18]([C:20]([NH:22][CH3:23])=[O:21])[O:19][C:15]=2[C:14]([N:5]2[CH2:6][CH2:7][C@H:3]([N:2]([CH3:8])[CH3:1])[CH2:4]2)=[C:13]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]=1[CH3:31])#[N:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 510423344-Cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

Product 1

HCID 510423364-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A dimethyl sulfoxide (1.5 ml) solution of (3S)-3-(dimethylamino)pyrrolidine (57 μl, 446 μmol) was added to a dimethyl sulfoxide (6 ml) solution of 4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-113) (115 mg, 372 μmol) and triethylamine (67 μl, 484 μmol) at 150° C., followed by stirring at the same temperature for 50 minutes under nitrogen atmosphere.

Sources & evidence

ORD record
ord-2d06679445ac4a608944ea9585a1256f
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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