N-methyl(3-methylbenzo[b]thiophen-2-yl)methanamine → (E)-3-(6-aminopyridin-3-yl)-N-methyl-N-(3-methylbenzo[b]thiophen-2-ylmethyl)acrylamide

HRID 1362228Notes

Reaction equation

HRID 1362228 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]=1[CH3:13].CNCC1C=CC2C(=CC=CC=2)C=1CCC.Cl.[NH2:31][C:32]1[N:37]=[CH:36][C:35](/[CH:38]=[CH:39]/[C:40]([OH:42])=O)=[CH:34][CH:33]=1>>[NH2:31][C:32]1[N:37]=[CH:36][C:35](/[CH:38]=[CH:39]/[C:40]([N:2]([CH3:1])[CH2:3][C:4]2[S:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[C:5]=2[CH3:13])=[O:42])=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 22593745N-methyl(3-methylbenzo[b]thiophen-2-yl)methanamineHCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineHCID 66967187(E)-3-(6-aminopyrid-3-yl)acrylic acid hydrochloride

Product 1

HCID 22593722(E)-3-(6-aminopyridin-3-yl)-N-methyl-N-(3-methylbenzo[b]thiophen-2-ylmethyl)acrylamideYield 73%

Procedure

According to the procedure of Example 1, except substituting methyl-(3-methyl-benzo[b]thiophen-2-ylmethyl)amine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, and substituting (E)-3-(6-amino-pyridin-3-yl)acrylic acid hydrochloride for the (E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3,-e][1,4]diazepin-7-yl)acrylic acid hydrochloride, the title compound (2.2 g, 73%) was prepared as a yellow solid: 1H NMR (300 MHz, DMSO-d6) 8.21 (s, 1H), 2.81-2.75 (m, 1H), 2.71-2.59 (m, 3H), 7.41-7.25 (m, 2H), 6.85-6.65 (m, 1H), 6.50-6.41 (m, 1H), 5.01-4.81 (m, 2H), 4.78-4.61 (m, 2H), 3.12 (s, 3H), 2.41 (s, 3H); MS (ESI) m/e 338 (M+H)+.

Sources & evidence

ORD record
ord-402c5c952588464e94eab55c9a0e4e2e
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…