Sodium Hydroxide → HCID 136166112, compound

HRID 243328Notes

Reaction equation

HRID 243328 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:16][N:17]2[C:21]3=[N:22][CH:23]=[N:24][C:25]([NH2:26])=[C:20]3[C:19]([C:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29](S(C4C=CC(C)=CC=4)(=O)=O)[CH:28]=3)=[N:18]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CCO>[NH:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27]([C:19]2[C:20]3[C:21](=[N:22][CH:23]=[N:24][C:25]=3[NH2:26])[N:17]([CH2:16][C:8]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=3)[N:18]=2)=[CH:28]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68158013HCID 68158013, compound

Product 1

HCID 136166112HCID 136166112, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine in EtOH (20 mL) was added NaOH (2 M, 20 mL). After stirred at room temperature overnight, the mixture was concentrated in vacuo. The residue was added H2O and extracted with CH2Cl2. The combined organic layers were evaporated and the residue was purified by P—HPLC to give 154 (500 mg, yield 51%) as a white solid. LCMS (ESI), M+H+=455.18. 1HNMR (400 MHz, DMSO) δ 5.891 (s, 2H), 7.033-7.068 (t, J=7 Hz, 1H), 7.111-7.186 (m, 2H), 7.233-7.284 (m, 2H), 7.458-7.513 (m, 6H), 7.622-7.642 (d, J=8 Hz, 1H), 7.682-7.703 (d, J=1.8 Hz, 1H), 7.724-7.731 (d, J=2.8 Hz, 1H), 8.367 (s, 1H), 11.639-11.644 (d, J=2 Hz, 1H)

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was added H2O
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layers were evaporated
  5. customthe residue was purified by P—HPLC

Sources & evidence

ORD record
ord-075ab319f7d44c9798c35679c8a537c4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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