tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-6-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate → N-(5-(6-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide

HRID 531520Notes

Reaction equation

HRID 531520 reaction equation
C(OC([N:8]([C:13]1[CH:14]=[C:15]([C:21]2[CH:22]=[C:23]3[C:32]([C:33]4[C:34]([CH3:47])=[N:35][N:36]([CH2:39][C:40]5[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=5)[C:37]=4[CH3:38])=[CH:31][N:30](C(OC(C)(C)C)=O)[C:24]3=[N:25][C:26]=2[CH:27]2[CH2:29][CH2:28]2)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[S:9]([CH3:12])(=[O:11])=[O:10])=O)(C)(C)C>Cl.O1CCOCC1>[CH:27]1([C:26]2[N:25]=[C:24]3[NH:30][CH:31]=[C:32]([C:33]4[C:34]([CH3:47])=[N:35][N:36]([CH2:39][C:40]5[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=5)[C:37]=4[CH3:38])[C:23]3=[CH:22][C:21]=2[C:15]2[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])[CH:14]=2)[CH2:28][CH2:29]1

Participants

4

Reactant 1

HCID 131735665tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-6-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 90031165N-(5-(6-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamideYield 18.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-6-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (60 mg, 0.078 mmol) was deprotected in HCl in 1,4-dioxane (2 ml). This afforded 8 mg (18.1% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 9.1-9.0 (b, 1H), 7.679-7.673 (d, 1H), 7.52 (s, 1H), 7.14-7.13 (d, 1H), 6.99-6.96 (m, 3H), 6.85 (m, 2H), 5.28 (s, 3H), 3.93 (s, 3H), 2.99 (s, 3H), 2.23 (s, 3H), 2.14 (s, 3H), 0.89-0.85 (m, 4H). MS: m/z=559.9 (M+1), HPLC: 85.5% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d4aa6d0a40a745279d4b0cb388f594b6
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…