tert-butyl 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(6-methoxy-5-(methyl sulfonamido)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate → HCID 178433947, compound

HRID 531586Notes

Reaction equation

HRID 531586 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[N:23][C:24]([O:32]C)=[C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:26]=4)[CH:19]=3)[N:14](C(OC(C)(C)C)=O)[CH:13]=2)[C:8]([CH3:41])=[N:7]1>Cl.CO>[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[C:25]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])[C:24]([OH:32])=[N:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:41])=[N:7]1

Participants

4

Reactant 1

HCID 90031029tert-butyl 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(6-methoxy-5-(methyl sulfonamido)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 178433947HCID 178433947, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(6-methoxy-5-(methylsulfonamido)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (61 mg, 0.098 mmol) was deprotected in HCl in MeOH (3 ml) to afford 5 mg (11.3% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.71-8.62 (d, 2H), 7.91-7.88 (d, 2H), 7.68 (s, 1H), 7.47-7.42 (m, 1H), 7.15-7.02 (m, 3H), 6.60 (s, 1H), 5.57 (s, 2H), 3.09 (s, 3H), 2.36 (s, 3H), 2.35 (s, 3H). MS: m/z=506.8 (M+1), HPLC: 90.22% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-32f85e790c2142cdafa75ae47331ddc0
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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