tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-fluorophenyl)-3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate → N-(5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)methanesulfonamide

HRID 531614Notes

Reaction equation

HRID 531614 reaction equation
C(OC([N:8]([C:13]1[CH:14]=[C:15]([C:20]2[CH:21]=[C:22]3[C:28]([C:29]4[C:30]([CH3:44])=[N:31][N:32]([CH2:35][C:36]5[CH:41]=[C:40]([F:42])[CH:39]=[C:38]([F:43])[CH:37]=5)[C:33]=4[CH3:34])=[CH:27][N:26](C(OC(C)(C)C)=O)[C:23]3=[N:24][CH:25]=2)[CH:16]=[CH:17][C:18]=1[F:19])[S:9]([CH3:12])(=[O:11])=[O:10])=O)(C)(C)C>Cl.O1CCOCC1.CO>[F:42][C:40]1[CH:41]=[C:36]([CH:37]=[C:38]([F:43])[CH:39]=1)[CH2:35][N:32]1[C:33]([CH3:34])=[C:29]([C:28]2[C:22]3[C:23](=[N:24][CH:25]=[C:20]([C:15]4[CH:16]=[CH:17][C:18]([F:19])=[C:13]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])[CH:14]=4)[CH:21]=3)[NH:26][CH:27]=2)[C:30]([CH3:44])=[N:31]1

Participants

4

Reactant 1

HCID 131735670tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-fluorophenyl)-3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 72944220N-(5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)methanesulfonamideYield 42.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21966525Dioxane MethanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-fluorophenyl)-3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (88 mg, 0.121 mmol) was deprotected in HCl in dioxane/MeOH (5/2 ml). This afforded 27 mg (35% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 13.6 (s, 1H), 8.42 (s, 1H), 8.26 (s, 1H), 7.80-7.77 (d, 1H), 7.50 (s, 1H), 7.33-7.32 (m, 2H), 6.79-6.69 (m, 4H), 5.33 (s, 2H), 3.09 (s, 3H), 2.24 (s, 3H), 2.18 (s, 3H). MS: m/z=526.2 (M+1), HPLC: 94.82% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-a9c88eac274941b6a6372f990d308678
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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