Water → HCID 86706436, compound

HRID 919553Notes

Reaction equation

HRID 919553 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20]3[C:21]4[CH:28]=[CH:27][N:26](S(C5C=CC(C)=CC=5)(=O)=O)[C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:14]2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1.O.C([O-])([O-])=O.[K+].[K+]>CO.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20]3[C:21]4[CH:28]=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:14]2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86706437HCID 86706437, compound

Product 1

HCID 86706436HCID 86706436, compoundYield 114.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(3-chloro-5-fluorophenylamino)-1-((S)-3-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl)ethanone (220 mg, 0.39 mmol) in MeOH:H2O (8:2 mL) was added K2CO3 (164 mg, 1.18 mmol) and the reaction mixture was heated to 60° C. for 1 h. The reaction mixture was concentrated in vacuo and the residue obtained was diluted with EtOAc. The EtOAc suspension was filtered through celite, the filtrate was then dried over Na2SO4, and concentrated in vacuo to give a residue that was subjected to purification by column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford the titled compound (180 mg, 83%). 1H NMR (400 MHz, CD3OD): δ 8.20 and 8.09 (2s, 1H), 7.06 (d, J=3.6 Hz, 1H), 6.61 and 6.58 (2d, J=3.6 Hz, 1H), 6.47 and 6.45 (2s, 1H), 6.35-6.27 (m, 2H), 4.97-4.79 (m, 2H), 4.25-3.95 (m, 3H), 3.11-3.05 (m, 1H), 2.95-2.86 (m, 1H), 2.14-1.85 (m, 2H), 1.80-1.55 (m, 2H). LC-MS: m/z [M+1]=403.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. filtrationThe EtOAc suspension was filtered through celite
  4. dry with materialthe filtrate was then dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a residue that
  7. customwas subjected to purification by column chromatography (silica gel, gradient MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-d4e99ea4f7d74ed0943fd01edd9a2fcd
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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