methyl((1-methyl-1H-indol-2-yl)methyl)amine → HCID 10347348, compound

HRID 1362194Notes

Reaction equation

HRID 1362194 reaction equation
[ClH:1].[NH2:2][C:3]1[N:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](O)=[O:12])=[CH:5][C:4]=1[CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]2[CH:27]=CC=[CH:24][CH:23]=2)[CH2:17][CH2:16]1.Cl.[CH3:29][N:30]1[CH2:36][C:35]2[CH:37]=[C:38](/[CH:41]=[CH:42]/[C:43](O)=O)C=N[C:34]=2[NH:33][C:32](=O)[CH2:31]1.CN[CH2:49][C:50]1N(C)C2C(C=1)=CC=CC=2.CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[ClH:1].[NH2:2][C:3]1[N:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([N:33]([CH3:34])[CH2:32][C:31]2[N:30]([CH3:29])[C:36]3[C:42]([CH:43]=2)=[CH:41][CH:38]=[CH:37][CH:35]=3)=[O:12])=[CH:5][C:4]=1[CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]2[CH:23]=[CH:24][CH:50]=[CH:49][CH:27]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 4

HCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 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 66967342HCID 66967342, compound

Product 1

HCID 10347348HCID 10347348, compoundYield 30%

Procedure

According to the procedure of Example 1, except substituting (E)-3-[6-amino-5-(4-benzyl-piperidin-1-ylmethyl)-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, and substituting methyl-(1-methyl-1H-indol-2-ylmethyl)amine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, the title compound (156 mg, 30%) was prepared as an off-white powder and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 8.36-8.25 (m, 2H), 7.52-6.98 (m, 14H), 6.40-6.15 (m, 1H), 5.05-4.84 (m, 2H), 4.20 (s, 2H), 3.74-3.67 (m, 3H), 3.58-5.30 (m, 8H), 3.10-2.73 (m, 6H); MS (ESI) m/e 508 (M+H)+.

Sources & evidence

ORD record
ord-3d37426ae6664429af1dd3e286a36ca6
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…