Toluene trifluoroacetic acid → N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-hydroxyethoxyl)phenyl)methanesulfonamide

HRID 531510Notes

Reaction equation

HRID 531510 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]3[C:26]([C:27]4[C:28]([CH3:41])=[N:29][N:30]([CH2:33][C:34]5[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=5)[C:31]=4[CH3:32])=[CH:25][N:24]([S:42]([C:45]4[CH:51]=[CH:50][C:48]([CH3:49])=[CH:47][CH:46]=4)(=[O:44])=[O:43])[C:21]3=[N:22][CH:23]=2)=[CH:14][C:13]=1[NH:52][S:53]([CH3:56])(=[O:55])=[O:54])C1C=CC=CC=1.C1(C)C=CC=CC=1.C(O)(C(F)(F)F)=O>>[F:40][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][CH:37]=1)[CH2:33][N:30]1[C:31]([CH3:32])=[C:27]([C:26]2[C:20]3[C:21](=[N:22][CH:23]=[C:18]([C:15]4[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][OH:8])=[C:13]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])[CH:14]=4)[CH:19]=3)[N:24]([S:42]([C:45]3[CH:46]=[CH:47][C:48]([CH3:49])=[CH:50][CH:51]=3)(=[O:44])=[O:43])[CH:25]=2)[C:28]([CH3:41])=[N:29]1

Participants

3

Reactant 2

HCID 69846924Toluene trifluoroacetic acidHCID 90034098N-(2-(2-(benzyloxy)ethoxy)-5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamide

Product 1

HCID 90031828N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-hydroxyethoxyl)phenyl)methanesulfonamide

Procedure

A stirred solution of N-(2-(2-(benzyloxy)ethoxy)-5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamide (120 mg, 0.151 mmol), toluene/TFA (5/5 ml) was heated to 70° C. for overnight. TLC showed reaction completion. Reaction mass was cooled to RT and solvents evaporated under reduced pressure. This afforded 152 mg of the crude titled compound. MS: m/z=704.2 (M+1).

Workup

  1. customreaction completion
  2. customReaction mass
  3. customsolvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-01d42310b88540d5b919df0b9ae234ea
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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