N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide → (E)-3-(6-Amino-5-morpholin-4-ylmethyl-pyridin-3-yl)-N-methyl-N-(1-methyl-1H-indol-3-ylmethyl)acrylamide

HRID 1362239Notes

Reaction equation

HRID 1362239 reaction equation
[CH3:1][N:2]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:17])[CH:9]=1)[C:3](=[O:6])[CH:4]=[CH2:5].CN(CC1SC2C=CC=CC=2C=1C)C(=O)C=C.Br[C:36]1[CH:37]=[C:38]([CH2:43][N:44]2[CH2:49][CH2:48][O:47][CH2:46][CH2:45]2)[C:39]([NH2:42])=[N:40][CH:41]=1.BrC1C=NC2NC(=O)C(C)(C)NCC=2C=1>>[NH2:42][C:39]1[N:40]=[CH:41][C:36](/[CH:5]=[CH:4]/[C:3]([N:2]([CH3:1])[CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:17])[CH:9]=2)=[O:6])=[CH:37][C:38]=1[CH2:43][N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1

Participants

5

Reactant 4

HCID 17930139N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamideHCID 22139011N-(1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamideHCID 594569147-Bromo-3,3-dimethyl-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-oneHCID 669662485-Bromo-3-morpholin-4-ylmethyl-pyridin-2-ylamine

Product 1

HCID 66967319(E)-3-(6-Amino-5-morpholin-4-ylmethyl-pyridin-3-yl)-N-methyl-N-(1-methyl-1H-indol-3-ylmethyl)acrylamideYield 38%

Procedure

According to the procedure of Example 2(a), except substituting N-methyl-N-(1-methyl-1H-indol-3-ylmethyl)acrylamide for the N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide, and substituting 5-bromo-3-morpholin-4-ylmethyl-pyridin-2-ylamine for the 7-bromo-3,3-dimethyl-1,3,4,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-2-one, the title compound (510 mg, 38%) was prepared as an off-white powder: 1H NMR (300 MHz, DMSO-d6) δ 8.13 (s, 1H),7.78 (s, 1H), 7.63-6.91 (m, 7H), 6.51 (s, 2H), 4.89-4.72 (m, 2H), 3.76 (s, 3H), 3.57 (br s, 4H), 3.42-3.34 (m, 2H), 3.02-2.90 (m, 3H), 2.33 (br s, 4H); MS (ESI) m/e 420 (M+H)+.

Sources & evidence

ORD record
ord-cd6e842b2d4749aebeb754545ee0d043
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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