Methanol → HCID 69676501, compound

HRID 919612Notes

Reaction equation

HRID 919612 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]([N:20]([CH3:30])[C:21]3[C:22]4[CH:29]=[CH:28][NH:27][C:23]=4[N:24]=[CH:25][N:26]=3)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.CO>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:19][CH:18]3[CH2:17][CH:14]2[CH:15]([N:20]([CH3:30])[C:21]2[C:22]4[CH:29]=[CH:28][NH:27][C:23]=4[N:24]=[CH:25][N:26]=2)[CH2:16]3)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 56968328HCID 56968328, compound

Product 1

HCID 69676501HCID 69676501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A similar procedure was used as describe for the synthesis of 2-(3,5-dichloro-phenylamino)-1-{3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-azepan-1-yl}-ethanone to afford a residue which was subjected to column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford (60 mg 45%) of the titled compound. 1H NMR (DMSO-d6, 400 MHz): 11.70 and 11.62 (2s, 1H), 8.20 and 8.12 (2s, 1H), 7.18-7.06 (m, 1H), 6.64 and 6.58 (2s, 2H), 6.62 and 6.54 (2s, 1H), 6.36-6.24 (m, 2H), 4.68 and 4.62 (2s, 1H), 3.96-3.72 (m, 1H), 3.60-3.52 (m, 2H), 3.18 and 3.16 (2s, 3H), 3.14-3.12 (m, 1H), 2.70-2.64 (m, 1H), 2.14-1.98 (m, 2H), 1.92-1.52 (m, 3H), LC-MS: m/z [M+1]=445.

Workup

  1. customto afford a residue which

Sources & evidence

ORD record
ord-b6fc261e2f0a4ec2967f4b365266503e
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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