N,N-Dimethylethylenediamine → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-(dimethylamino)ethylamino)thieno[2,3-b]pyrazine-6-carboxamide
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].ClC1N=C2SC(C(NC3C=C(NC(=O)C4C=CC=C(C(C#N)(C)C)C=4)C=CC=3C)=O)=CC2=NC=1.NC[CH2:72][N:73]([CH3:75])[CH3:74]>>[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][CH2:30][CH2:72][N:73]([CH3:75])[CH3:74])=[CH:27][N:28]=[C:23]3[CH:22]=2)=[O:20])[CH:17]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]Participants
4
Reactant 3
Product 1
Procedure
Preparation analogous to 96a 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 1-amino-2-dimethylaminoethane (1.531 mmol, 167 μL, 135 mg) to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-(dimethylamino)ethylamino)thieno[2,3-b]pyrazine-6-carboxamide 96c (12 mg, 36%). NMR (400 MHz, DMSO-d6) 1.75 (s, 6H), 2.22 (s, 6H), 2.24 (s, 3H), 3.45 (q, J=5.9 Hz, 2H), 7.28 (d, J=8.2 Hz, 1H), 7.61 (m, 2H), 7.75 (m, 2H), 7.82 (d, J=2.0 Hz, 1H), 7.95 (d, J=7.4 Hz, 1H), 8.05 (s, 1H), 8.19 (s, 1H), 8.24 (s, 1H), 10.07 (s, 1H), 10.33 (s, 1H). (m/z)=542 (M+H)+.
Sources & evidence
- ORD record
- ord-93b6fd6521a2400bbacc1d9e41d21a9d
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669256B2
Reaction notes
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