Methanol → HCID 68070459, compound

HRID 919611Notes

Reaction equation

HRID 919611 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]([NH:20][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:16]2[CH:15]([NH:20][C:21]2[C:22]4[CH:29]=[CH:28][NH:27][C:23]=4[N:24]=[CH:25][N:26]=2)[CH2:14]3)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 86706474HCID 86706474, compound

Product 1

HCID 68070459HCID 68070459, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A similar procedure was used as describe for the synthesis of 2-(3,5-dichlorophenylamino)-1-(3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino) azepan-1-yl) ethanone to afford a residue which was subjected to column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford (45 mg, 51%) the titled compound. 1H NMR (DMSO-d6, 400 MHz): 11.50 and 11.40 (2s, 1H), 8.18-8.10 (2s, 1H), 7.18 (bs, 1H), 7.08 (bs, 1H), 6.66 and 6.60 (2s, 2H), 6.58 and 6.50 (2s, 1H), 6.21 and 6.08 (2s, 2H), 4.62 and 4.46 (2s, 1H), 3.88-3.48 (m, 2H), 3.10-2.90 (m, 2H), 2.72-2.50 (m, 1H), 2.24-2.10 (m, 2H), 1.82-1.62 (m, 3H). LC-MS: m/z [M+1]=431.

Workup

  1. customto afford a residue which

Sources & evidence

ORD record
ord-14c6caac1866418aa409f13b761e881c
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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