Dimethylamine → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(dimethylamino)thieno[2,3-b]pyrazine-6-carboxamide

HRID 1184904Notes

Reaction equation

HRID 1184904 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:33]=[CH:34][CH:35]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:32])=[C:16]([NH:18][C:19]([C:21]2[S:31][C:24]3=[N:25][C:26]([NH:29][CH3:30])=[CH:27][N:28]=[C:23]3[CH:22]=2)=[O:20])[CH:17]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].Cl[C:37]1N=C2SC(C(NC3C=C(NC(=O)C4C=CC=C(C(C#N)(C)C)C=4)C=CC=3C)=O)=CC2=NC=1.CNC.C1COCC1>>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:33]=[CH:34][CH:35]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:32])=[C:16]([NH:18][C:19]([C:21]2[S:31][C:24]3=[N:25][C:26]([N:29]([CH3:37])[CH3:30])=[CH:27][N:28]=[C:23]3[CH:22]=2)=[O:20])[CH:17]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 67125590N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(methylamino)thieno[2,3-b]pyrazine-6-carboxamideHCID 866801803-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

Product 1

HCID 67125650N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(dimethylamino)thieno[2,3-b]pyrazine-6-carboxamideYield 9%

Procedure

Preparation analogous to 96a (step 11) by using 3-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 95 (0.061 mmol, 30 mg) and dimethylamine 2M in THF (1.531 mmol, 765 μL) to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(dimethylamino)thieno[2,3-b]pyrazine-6-carboxamide 96b (3 mg, 9%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.25 (s, 3H), 3.20 (s, 6H), 7.28 (d, J=8.6 Hz, 1H), 7.61 (m, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.84 (d, J=2.0 Hz, 1H), 7.95 (d, J=7.8 Hz, 1H), 8.05 (s, 1H), 8.30 (s, 1H), 8.43 (s, 1H), 10.13 (s, 1H), 10.35 (s, 1H). (m/z)=499 (M+H)+.

Sources & evidence

ORD record
ord-a8deee186bec4929a8a8651562f4f28e
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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