tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate → N-(2-methoxy-5-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

HRID 531597Notes

Reaction equation

HRID 531597 reaction equation
C(OC([N:8]([C:13]1[CH:14]=[C:15]([C:21]2[CH:22]=[C:23]3[C:29]([C:30]4[CH:31]=[N:32][N:33]([CH2:35][C:36]5[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=5)[CH:34]=4)=[CH:28][N:27](C(OC(C)(C)C)=O)[C:24]3=[N:25][CH:26]=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.CCOCC.CO>[CH3:20][O:19][C:18]1[CH:17]=[CH:16][C:15]([C:21]2[CH:22]=[C:23]3[C:29]([C:30]4[CH:31]=[N:32][N:33]([CH2:35][C:36]5[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=5)[CH:34]=4)=[CH:28][NH:27][C:24]3=[N:25][CH:26]=2)=[CH:14][C:13]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

4

Reactant 1

HCID 131735669tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 72944104N-(2-methoxy-5-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamideYield 29%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 5-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxyphenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (60 mg, 0.219 mmol) was deprotected in HCl in ether/MeOH (1/3 ml) to afford 13 mg (29% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.78 (s, 2H), 8.53 (s, 2H), 8.42-8.37 (m, 2H), 8.02 (s, 1H), 8.00-7.94 (m, 1H), 7.77-7.76 (m, 2H), 7.62-7.59 (dd, 1H), 7.24-7.21 (d, 1H), 5.66 (s, 2H), 3.98 (s, 3H), 2.99 (s, 3H). MS: m/z=475.1 (M+1), HPLC: 97.36% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-6f63cde017654931b5a99137141d65ee
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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