2-Morpholinoethylamine → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-morpholinoethylamino)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]1[CH2:78][CH2:77][O:76][CH2:75][CH2:74]1>>[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]4[CH2:78][CH2:77][O:76][CH2:75][CH2:74]4)=[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 4-(2-aminoethyl)morpholine (1.531 mmol, 201 μL) to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-morpholinoethylamino)thieno[2,3-b]pyrazine-6-carboxamide 96e (12 mg, 34%). NMR (400 MHz, DMSO-d6) 1.75 (s, 6H), 2.24 (s, 3H), 2.46 (br s, 4H), 2.56 (br s, 2H), 3.50 (br s, 2H), 3.60 (br s, 4H), 7.28 (d, J=8.6 Hz, 1H), 7.61 (m, 2H), 7.75 (m, 2H), 7.83 (d, J=2.0 Hz, 1H), 7.94 (d, J=7.8 Hz, 1H), 8.05 (s, 1H), 8.18 (s, 1H), 8.25 (s, 1H), 10.08 (s, 1H), 10.33 (s, 1H). (m/z)=584 (M+H)+.
Sources & evidence
- ORD record
- ord-de06f3f821fe492494afc16d48a10dac
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669256B2
Reaction notes
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