Triethylamine → 2-(N-tert-Butyl-N-methylamino)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17412Notes

Reaction equation

HRID 17412 reaction equation
[C:1]([N:5]([C:7]1[O:8][C:9]2[C:10](=[C:12]([C:24]#[N:25])[C:13]([CH3:23])=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15]=2F)[N:11]=1)[CH3:6])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][NH:37][CH2:36]1>CS(C)=O>[C:1]([N:5]([C:7]1[O:8][C:9]2[C:10](=[C:12]([C:24]#[N:25])[C:13]([CH3:23])=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15]=2[N:37]2[CH2:38][CH2:39][C@H:35]([N:34]([CH3:40])[CH3:33])[CH2:36]2)[N:11]=1)[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685839942-(N-tert-butyl-N-methylamino)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685857652-(N-tert-Butyl-N-methylamino)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

2-(N-tert-butyl-N-methylamino)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-137) (0.22 g, 0.65 mmol) was suspended in dimethyl sulfoxide (5 ml), then triethylamine (0.19 ml, 1.37 mmol) and (3S)-3-(dimethylamino)pyrrolidine (0.17 ml, 1.34 mmol) were added, followed by stirring in a sealed tube at an external temperature of about 150° C. for 4 hours.

Sources & evidence

ORD record
ord-87b0b719671b47aba6b796668a5ddd4f
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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