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

HRID 1184910Notes

Reaction equation

HRID 1184910 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:46](NC3C=C(NC(=O)C4C=CC=C(C(C#N)(C)C)C=4)C=CC=3C)=[O:47])=CC2=NC=1.NCCO>>[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][CH2:46][OH:47])=[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

HCID 700EthanolamineHCID 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 67125645N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-hydroxyethylamino)thieno[2,3-b]pyrazine-6-carboxamideYield 15%

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 2-aminoethanol (1.53 mmol, 92 μL). The crude compound was purified by HPLC and the chromatography (0-10 methanol in CH2Cl2) to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-hydroxyethylamino)thieno[2,3-b]pyrazine-6-carboxamide 96h (5 mg, 15%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.24 (s, 3H), 3.44 (q, J=5.9 Hz and 5.1 Hz, 2H), 3.59 (q, J=5.9 Hz and 5.1 Hz, 2H), 4.83 (t, J=5.1 Hz, 1H), 7.28 (d, J=8.6 Hz, 1H), 7.60 (m, 2H), 7.75 (m, 1H), 7.83 (d, J=2.0 Hz, 1H), 7.89 (m, 1H), 7.95 (d, J=7.8 Hz, 1H), 8.05 (s, 1H), 8.17 (s, 1H), 8.25 (s, 1H), 10.08 (s, 1H), 10.34 (s, 1H). (m/z)=516 (M+H)+.

Workup

  1. customThe crude compound was purified by HPLC

Sources & evidence

ORD record
ord-c4e24a39eeb74fa6a5d95ce209b12d7e
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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