Methanol → HCID 68070550, compound

HRID 919613Notes

Reaction equation

HRID 919613 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]([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>[N:24]1[C:23]2[NH:27][CH:28]=[CH:29][C:22]=2[C:21]([NH:20][CH:15]2[CH2:14][N:13]([C:11](=[O:12])[CH2:10][NH:9][C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)[CH2:19]2)=[N:26][CH:25]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 86706474HCID 86706474, compound

Product 1

HCID 68070550HCID 68070550, 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 give a residue, that was subjected to column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford (107 mg, 51%) the titled compound. 1H NMR (DMSO-d6, 400 MHz): 11.70 (s, 1H), 8.14 (s, 1H), 7.96 (d, J=2.0 Hz, 1H), 7.16 (s, 1H), 6.64 (s, 3H), 6.56 (s, 1H), 6.40 (bs, 1H), 4.94-4.80 (m, 1H), 4.58 (t, J=8.0 Hz, 1H), 4.30 (t, J=8.0 Hz, 1H), 4.16-4.04 (m, 1H), 3.98-3.86 (m, 1H), 3.78 (d, J=1.6 Hz, 2H). LC-MS: m/z [M+1]=391.

Workup

  1. customto give a residue, that

Sources & evidence

ORD record
ord-c3ac0302ac68425cba82808b50ee8a87
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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