(S)-1-(4-(5-(3-(1-(3-(benzyloxy)benzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol → (S)-3-((4-(5-(6-(4-(2-hydroxypropyl)piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrazol-1-yl)methyl)phenol

HRID 531800Notes

Reaction equation

HRID 531800 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:53]=[CH:54][CH:55]=1)[CH2:12][N:13]1[CH:17]=[C:16]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[C:24]([C:27]4[CH:28]=[CH:29][C:30]([N:33]5[CH2:38][CH2:37][N:36]([CH2:39][C@@H:40]([OH:42])[CH3:41])[CH2:35][CH2:34]5)=[N:31][CH:32]=4)[CH:25]=3)[N:20]([S:43]([C:46]3[CH:52]=[CH:51][C:49]([CH3:50])=[CH:48][CH:47]=3)(=[O:45])=[O:44])[CH:19]=2)[CH:15]=[N:14]1)C1C=CC=CC=1>C1(C)C=CC=CC=1.C(O)(C(F)(F)F)=O>[OH:42][C@@H:40]([CH3:41])[CH2:39][N:36]1[CH2:37][CH2:38][N:33]([C:30]2[N:31]=[CH:32][C:27]([C:24]3[CH:25]=[C:26]4[C:18]([C:16]5[CH:15]=[N:14][N:13]([CH2:12][C:11]6[CH:10]=[C:9]([OH:8])[CH:55]=[CH:54][CH:53]=6)[CH:17]=5)=[CH:19][N:20]([S:43]([C:46]5[CH:47]=[CH:48][C:49]([CH3:50])=[CH:51][CH:52]=5)(=[O:44])=[O:45])[C:21]4=[N:22][CH:23]=3)=[CH:28][CH:29]=2)[CH2:34][CH2:35]1

Participants

3

Reactant 1

HCID 90030702(S)-1-(4-(5-(3-(1-(3-(benzyloxy)benzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol

Product 1

HCID 118524116(S)-3-((4-(5-(6-(4-(2-hydroxypropyl)piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrazol-1-yl)methyl)phenol

Reagents, catalysts & solvents 1

HCID 69846924Toluene trifluoroacetic acidSolvent

Procedure

To the solution of (S)-1-(4-(5-(3-(1-(3-(benzyloxy)benzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol (200 mg, 0265 mmol) in toluene/TFA (10/5 mL) was heated at 100° C. for 16 hours and distilled out the solvent. This was basified with triethylamine and distilled out the solvent to get 180 mg (crude) of the titled compound. MS: m/z=664.2 (M+1).

Workup

  1. distillationdistilled out the solvent
  2. distillationdistilled out the solvent

Sources & evidence

ORD record
ord-98b89a35602d4ab2bcd96b6a9a805541
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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