Hydrochloride methanol → N-(5-(2-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide

HRID 531524Notes

Reaction equation

HRID 531524 reaction equation
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([N:25](C(OC(C)(C)C)=O)[S:26]([CH3:29])(=[O:28])=[O:27])[CH:18]=3)[CH:16]=[C:11]2[C:10]([C:37]2[C:38]([CH3:51])=[N:39][N:40]([CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[CH:45]=3)[C:41]=2[CH3:42])=[C:9]1[CH:52]1[CH2:54][CH2:53]1)=O)(C)(C)C.CO.Cl>>[CH:52]1([C:9]2[NH:8][C:12]3=[N:13][CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:18]=4)[CH:16]=[C:11]3[C:10]=2[C:37]2[C:38]([CH3:51])=[N:39][N:40]([CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[CH:45]=3)[C:41]=2[CH3:42])[CH2:54][CH2:53]1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 131735666tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-2-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 72943389N-(5-(2-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamideYield 8.18%

Procedure

tert-butyl5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-2-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (150 mg) was hydrolyzed with methanol/HCl (5 ml) at 0° C. and purified by prep HPLC to afford 9 mg (8.18% yield) of the pure required product. 1H NMR (CD3OD, 400 MHz): δ 8.32-8.31 (s, 1H), 7.65-7.64 (d, 1H), 7.54-7.7.53 (d, 1H), 7.42-7.37 (q, 1H), 7.06-6.94 (m, 3H), 6.88-6.86 (d, 1H), 5.39 (s, 2H), 3.85 (s, 3H), 3.82 (s, 3H), 2.14 (s, 3H), 2.04 (s, 3H), 1.94-1.93 (m, 1H), 1.04-0.90 (m, 4H). MS: m/z=560.0 (M+1), HPLC Purity: 78.69% Method: B.

Workup

  1. custompurified by prep HPLC

Sources & evidence

ORD record
ord-bd676de5eaa24bb7a84638cf65f1e9b2
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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