N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine → HCID 59277609, compound

HRID 2097111Notes

Reaction equation

HRID 2097111 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH3:13].[CH3:14][N:15]1[CH2:21][C:20]2[CH:22]=[C:23]([CH:26]=[CH:27][C:28](O)=[O:29])[CH:24]=[N:25][C:19]=2[NH:18][C:17](=[O:31])[CH2:16]1>>[CH3:1][N:2]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH3:13])[C:28](=[O:29])/[CH:27]=[CH:26]/[C:23]1[CH:24]=[N:25][C:19]2[NH:18][C:17](=[O:31])[CH2:16][N:15]([CH3:14])[CH2:21][C:20]=2[CH:22]=1

Participants

3

Reactant 2

HCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amineHCID 669662013-(4-Methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylic acid

Product 1

HCID 59277609HCID 59277609, compoundYield 9.9%

Procedure

According to the method of example 35g, methyl-(2-methyl-1H-indol-3-ylmethyl)amine (115 mg, 0.66 mmol) and 3-(4-Methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylic acid (192 mg, 0.6 mmol) were coupled to give crude product. Purification by column chromatography (silica gel, CH2Cl2/MeOH/NH3, 9:4.55:0.05) gave title compound (24 mg, 9%) as a white solid and as a mixture of amide rotomers. 1H NMR (300 MHz, DMSO-d6) δ 8.48 (s, 1H), 7.95-8.01 (m, 2H), 7.56-7.60 (m, 2H), 7.47-7.50 (m, 1H), 7.16-7.26 (m, 2H), 6.92-7.05 (m, 2H), 3.90 (s, 2H), 3.56 (s, 2H), 3.02 (s, 2H), 2.93 (s, 3H), 2.83 (s, 3H), 2.46 (s, 3H); MS (EST) m/e 404 (C23H25N5O2+H)+.

Workup

  1. customto give crude product
  2. customPurification by column chromatography (silica gel, CH2Cl2/MeOH/NH3, 9:4.55:0.05)

Sources & evidence

ORD record
ord-fa62906608a84a9c92eace4ff2261536
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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