N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine → HCID 16660474, compound

HRID 2097110Notes

Reaction equation

HRID 2097110 reaction equation
[CH3:1][N:2]1[CH2:8][C:7]2[CH:9]=[C:10]([CH:13]=[CH:14][C:15]([OH:17])=O)[CH:11]=[N:12][C:6]=2[NH:5][CH2:4][C:3]1=[O:18].[CH3:19][NH:20][CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][C:23]=1[CH3:31]>>[CH3:19][N:20]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][C:23]=1[CH3:31])[C:15](=[O:17])/[CH:14]=[CH:13]/[C:10]1[CH:11]=[N:12][C:6]2[NH:5][CH2:4][C:3](=[O:18])[N:2]([CH3:1])[CH2:8][C:7]=2[CH:9]=1

Participants

3

Reactant 2

HCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amineHCID 66967097HCID 66967097, compound

Product 1

HCID 16660474HCID 16660474, compound

Procedure

According to the method of example 35g, 3-(4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylic acid (69 mg, 0.28 mmol) and methyl-(2-methyl-1H-indol-3-ylmethyl)amine (60 mg, 0.34 mmol) were coupled to yield the title compound as a white powder and as a mixture of amide rotomers (40 mg, 35%). 1H NMR (300 MHz, DMSO-d6) 10.86 (s, 1H), 8.12 (bs, 1H), 7.77 (bs, 1H), 7.49-7.41 (m, 2H), 7.34-7.30 (m, 1H), 7.25-7.22 (m, 1H), 7.00-6.85 (m, 3H), 4.84-4.71 (m, 2H), 4.53 (s, 2H), 4.09-4.07 (m, 2H), 2.93-2.91 (m, 6H), 2.40 (bs, 3H); ESI MS m/z 404.

Sources & evidence

ORD record
ord-0a119d427ff54c6ba6f15f6a4109df6d
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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