Methanol → HCID 68070445, compound

HRID 919614Notes

Reaction equation

HRID 919614 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:19]CCC[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:8][C:6]1[CH:5]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:14][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)[CH2:19]2)=[O:12])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 56968328HCID 56968328, compound

Product 1

HCID 68070445HCID 68070445, compoundYield 23%

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 give a residue that was subjected to column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford (10 mg, 23%) the titled compound. 1H NMR (DMSO-d6, 400 MHz): 11.88 (bs, 1H), 8.18 (s, 1H), 7.22 (d, J=4.0 Hz, 1H), 6.66 (s, 2H), 6.60 (s, 1H), 6.50-6.22 (m, 1H), 5.58-5.42 (m, 1H), 4.54 (t, J=8.0 Hz, 2H), 4.40-4.28 (m, 1H), 4.24 (t, J=8.0 Hz, 1H), 4.16-4.08 (m, 1H), 3.36 (s, 3H) 3.80 (d, J=2.0 Hz, 1H). LC-MS: m/z [M+1]=405.

Workup

  1. customto give a residue that

Sources & evidence

ORD record
ord-a83d41baa9ac45a8a434cab7f240bb80
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

Loading…