Potassium Hydroxide → HCID 44467741, compound

HRID 2281379Notes

Reaction equation

HRID 2281379 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[CH:31]=[CH:30][N:29](S(C4C=CC(C)=CC=4)(=O)=O)[C:9]=3[N:10]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][N:23]([C:26](=[O:28])[CH3:27])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:12]=2)[CH2:3]1.[OH-].[K+]>CO>[N:20]1([C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:11]3[N:12]=[C:7]([N:4]4[CH2:5][CH2:6][C@H:2]([OH:1])[CH2:3]4)[C:8]4[CH:31]=[CH:30][NH:29][C:9]=4[N:10]=3)=[CH:15][CH:16]=2)[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]1.[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[CH:31]=[CH:30][NH:29][C:9]=3[N:10]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][N:23]([C:26](=[O:28])[CH3:27])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:12]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57990284HCID 57990284, compound

Product 2

HCID 44467741HCID 44467741, compoundHCID 44467742HCID 44467742, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-1-(4-(4-(4-(3-hydroxypyrrolidin-1-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (80 mg, 0.14 mmol) in MeOH (3 mL), aq. 1N KOH (1 mL) was added. It was stirred at 60° C. for 4 h. After being concentrated in vacuo, the residue was acidified with HOAc (1 mL). The mixture was then purified by HPLC to give (S)-1-(2-(4-(piperazin-1-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-ol (5 mg) (MS 380.5 (M+H)) and (S)-1-(4-(4-(4-(3-hydroxypyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (20 mg) (MS 422.5 (M+H)).

Workup

  1. concentrationAfter being concentrated in vacuo
  2. customThe mixture was then purified by HPLC

Sources & evidence

ORD record
ord-0bd752afdd024c0f992f76f77cf87cf5
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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