Methanol → HCID 56968328, compound

HRID 919610Notes

Reaction equation

HRID 919610 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]([CH3:40])[C:21]3[C:22]4[CH:29]=[CH:28][N:27](S(C5C=CC(C)=CC=5)(=O)=O)[C:23]=4[N:24]=[CH:25][N:26]=3)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].CO>CO.O.C(Cl)Cl>[Cl:8][C:6]1[CH:5]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]([N:20]([CH3:40])[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:3]=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 118890590HCID 118890590, compound

Product 1

HCID 56968328HCID 56968328, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(3,5-dichloro-phenylamino)-1-(3-{methyl-[7-(tosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amino}-azepan-1-yl)-ethanone (235 mg. 0.39 mmol) in MeOH:H2O (4:1, 5 mL) was added K2CO3 (216 mg, 1.56 mmol) and heated at 90° C. for 1 h. The reaction mixture was cooled to rt and concentrated in vacuo to give a residue which was subjected to column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford the titled compound (80.6 mg, 46%). 1H NMR (DMSO-d6, 400 MHz): 11.60 (1s, 1H), 8.08 (s, 1H), 7.12 (d, J=4 Hz, 1H), 6.72 (s, 1H), 6.69 (s, 1H), 6.63 (s, 1H), 6.62 (s, 1H), 6.38-6.35 (m, 1H), 4.98-4.85 (m, 1H), 4.29 and 1.28 (2d, J=2.1 Hz, 1H), 4.10-3.88 (m, 3H), 3.65-2.32 (m, 2H), 3.17 (s, 3H), 1.93-1.76 (m, 6H). LC-MS: m/z [M+1]=447.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated in vacuo
  3. customto give a residue which

Sources & evidence

ORD record
ord-d3a3c7c8db12425b9b92ec2d28aea943
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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