N-methyl(3-methylbenzo[b]thiophen-2-yl)methanamine → HCID 10005048, compound

HRID 1711888Notes

Reaction equation

HRID 1711888 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=O)=[CH:4][C:3]=1[CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[ClH:20].CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1.[CH3:39][NH:40][CH2:41][C:42]1[S:46][C:45]2[CH:47]=[CH:48][CH:49]=[CH:50][C:44]=2[C:43]=1[CH3:51].CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[ClH:20].[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:40]([CH3:39])[CH2:41][C:42]2[S:46][C:45]3[CH:47]=[CH:48][CH:49]=[CH:50][C:44]=3[C:43]=2[CH3:51])=[O:12])=[CH:4][C:3]=1[CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 22593745N-methyl(3-methylbenzo[b]thiophen-2-yl)methanamineHCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineHCID 66966197(E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochlorideHCID 66966290HCID 66966290, compound

Product 1

HCID 10005048HCID 10005048, compoundYield 67%

Procedure

According to the procedure of Example 1, except substituting (E)-3-(6-amino-5-morpholin-4-ylmethyl-pyridin-3-yl)acrylic acid 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, and substituting methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)amine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, the title compound (111 mg, 67%) was prepared as a pale, yellow solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 8.60 (br s, 1H), 8.40 (s, 1H), 7.87 (d, J=7.4 Hz, 1H), 7.73 (d, J=6.9 Hz, 1H), 7.51 (d, J=15.3 Hz, 1H), 7.42-7.15 (m, 3H), 5.12-4.88 (m, 2H), 3.91-3.35 (m, 12H), 3.15 (s, 3H), 2.93 (s, 1H), 2.41 (s, 3H); MS (ESI) m/e 437 (M+H)+;

Sources & evidence

ORD record
ord-b03a57bddd51430b826dcee98e418f31
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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