HCID 118524084, compound → HCID 72943387, compound

HRID 531518Notes

Reaction equation

HRID 531518 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]3[N:10](C(OC(C)(C)C)=O)[CH:11]=[C:12]([C:13]4[C:14]([CH3:28])=[N:15][N:16]([CH2:19][C:20]5[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=5)[C:17]=4[CH3:18])[C:7]3=[CH:6][C:5]=2[C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])[CH:37]=2)[CH2:3][CH2:2]1>Cl.O1CCOCC1>[CH:1]1([C:4]2[N:9]=[C:8]3[NH:10][CH:11]=[C:12]([C:13]4[C:14]([CH3:28])=[N:15][N:16]([CH2:19][C:20]5[CH:21]=[C:22]([F:27])[CH:23]=[C:24]([F:26])[CH:25]=5)[C:17]=4[CH3:18])[C:7]3=[CH:6][C:5]=2[C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([NH:44][S:45]([CH3:48])(=[O:46])=[O:47])[CH:37]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 118524084HCID 118524084, compound

Product 1

HCID 72943387HCID 72943387, compoundYield 9.1%

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 6-cyclopropyl-3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-methoxy-3-(methylsulfonamido)phenyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (70 mg, 0.103 mmol) was deprotected in HCl in 1,4-dioxane (2 ml). This afforded 5 mg (9.1% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.24 (s, 1H), 7.66 (s, 1H), 7.59-7.58 (m, 1H), 7.38-7.34 (dd, 1H), 7.22-7.19 (m, 1H), 6.93-6.90 (m, 1H), 6.82-6.76 (m, 1H), 5.45-5.39 (t, 2H), 3.96 (s, 3H), 2.94 (s, 3H), 2.5-2.4 (m, 1H), 2.25 (s, 3H), 1.4-1.0 (m, 4H). MS: m/z=538.1 (M+1), HPLC: 81% method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-9a108c29e16a4b0296ed8e7b88a4656d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…