HCID 118524093, compound → HCID 72944956, compound

HRID 531888Notes

Reaction equation

HRID 531888 reaction equation
[CH2:1]([N:9]1[CH:13]=[C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][C:26]([N:29]5[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]5)=[CH:25][CH:24]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH:11]=[N:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>Cl>[CH2:1]([N:9]1[CH:13]=[C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][C:26]([N:29]5[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]5)=[CH:25][CH:24]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH:11]=[N:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 118524093HCID 118524093, compound

Product 1

HCID 72944956HCID 72944956, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(4-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (130 mg, 0.238 mmol) was deprotected in methanolic HCl (5 ml). This afforded 78 mg (58.6% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.49 (s, 1H), 8.327-8.322 (d, 1H), 7.878-7.876 (d, 1H), 7.788-7.7.87 (d, 1H), 7.672-7.644 (m, 3H), 7.23-7.12 (m, 7H), 4.47-4.43 (t, 2H), 3.52-3.49 (m, 4H), 3.43-3.40 (m, 4H), 3.20-3.17 (t, 2H). MS: m/z=449.4 (M+1), HPLC: 95.50% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-1ce0ad50e65e493dbc8cc4b2dc911870
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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