Potassium Hydroxide → HCID 57990428, compound

HRID 2281455Notes

Reaction equation

HRID 2281455 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[C:13]3[CH:32]=[CH:31][N:30](S(C4C=CC(C)=CC=4)(=O)=O)[C:14]=3[N:15]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]([CH3:29])[C:26](=[O:28])[CH3:27])=[CH:21][CH:20]=3)[N:17]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[OH-].[K+]>CO>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[C:13]3[CH:32]=[CH:31][NH:30][C:14]=3[N:15]=[C:16]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([N:25]([CH3:29])[C:26](=[O:28])[CH3:27])=[CH:23][CH:24]=3)[N:17]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66878065N-(4-(4-(3-aminosulfonyl-phenylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide

Product 1

HCID 57990428HCID 57990428, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(4-(4-(3-aminosulfonyl-phenylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide (20 mg, 0.033 mmol) in MeOH (2 mL), aq. 1N KOH (0.60 mL, 0.60 mmol) was added. The mixture was heated 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 (7 mg). MS 452.0 (M+H); UV 208.5, 284.1, 317.4 nm.

Workup

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

Sources & evidence

ORD record
ord-39f22ea42425431492c45e5714b7ead6
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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