Potassium Hydroxide → N-(4-(4-(3-(aminomethyl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide

HRID 2281488Notes

Reaction equation

HRID 2281488 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:11]3[CH:30]=[CH:29][N:28](S(C4C=CC(C)=CC=4)(=O)=O)[C:12]=3[N:13]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]([CH3:27])[C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=3)[N:15]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[K+]>CO>[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:11]3[CH:30]=[CH:29][NH:28][C:12]=3[N:13]=[C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([N:23]([CH3:27])[C:24](=[O:26])[CH3:25])=[CH:21][CH:22]=3)[N:15]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57990342N-(4-(4-(3-(aminomethyl)phenylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide

Product 1

HCID 44467954N-(4-(4-(3-(aminomethyl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamideYield 76.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(4-(4-(3-(aminomethyl)phenylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide (27 mg, 0.049 mmol) in MeOH (3 mL), aq. 1N KOH (1.0 mL, 1.0 mmol) was added. The mixture was stirred at 60° C. for 3 h. It was concentrated in vacuo. The residue was acidified with HOAc (1 mL) before being purified by HPLC to give the titled compound (15 mg). MS 402.3 (M+H); UV 202.6, 282.9, 315.0 nm.

Workup

  1. concentrationIt was concentrated in vacuo
  2. custombefore being purified by HPLC

Sources & evidence

ORD record
ord-441507200c2f4e24832a2423d5d95234
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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