Methanol → HCID 86706474, compound

HRID 919608Notes

Reaction equation

HRID 919608 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][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]([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:3]=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86706475HCID 86706475, compound

Product 1

HCID 86706474HCID 86706474, compoundYield 66.7%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(3,5-dichlorophenylamino)-1-(3-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)azepan-1-yl)ethanone (800 mg, 1.36 mmol) in MeOH:H2O (4:1, 5 mL) was added K2CO3 (656 mg, 4.77 mmol) and the reaction mixture was heated at 80° C. for 4 h. The reaction mixture was concentrated in vacuo to give a residue which was triturated with 10% MeOH in EtOAc (20 mL), filtrated, the filtrate was evaporated in vacuo to give the crude compound that was subjected to column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford (393 mg, 66%) the titled compound. 1H NMR (DMSO-do, 400 MHz): 11.53 and 11.47 (2s, 1H), 8.15 and 8.07 (2s, 1H), 7.30 and 7.17 (2d, J=4 Hz, 1H), 7.07 (2t, d=2.4 Hz, 1H), 6.74 (s, 1H), 6.68 (m, 1H), 6.62 (s, 1H), 6.38-6.33 (m, 1H), 4.54-4.46 (m, 1H), 4.36-4.27 (m, 1H), 4.12-3.96 (m, 2H), 3.94-3.86 (m, 1H), 3.52-3.42 (m, 1H), 3.24-3.12 (m, 1H), 2.02-1.78 (m, 3H), 1.74-1.52 (m, 3H). LC-MS: m/z [M+1]=433.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a residue which
  3. customwas triturated with 10% MeOH in EtOAc (20 mL)
  4. filtrationfiltrated
  5. customthe filtrate was evaporated in vacuo
  6. customto give the crude compound that

Sources & evidence

ORD record
ord-bc730ebfc5c2433e812dcc762f993a2d
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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