HCID 118523932, compound → HCID 90031531, compound

HRID 531659Notes

Reaction equation

HRID 531659 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:24]=[C:25]([CH:40]=[CH:41][CH:42]=4)[O:26][CH:27]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]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.CO>[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:42]=[CH:41][CH:40]=[C:25]([O:26][CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)[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

4

Reactant 1

HCID 118523932HCID 118523932, compound

Product 1

HCID 90031531HCID 90031531, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(3-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenoxy)piperidine-1-carboxylate (80 mg, 0.142 mmol) was deprotected in HCl in methanol (5 ml). This afforded 31 mg (37.7% yield) of the titled compound after purification by preparative HPLC. 1H NMR (CD3OD, 400 MHz): δ 8.70-8.50 (bs, 1H), 8.32 (s, 1H), 7.89 (s, 1H), 7.79 (s, 1H), 7.65 (s, 1H), 7.52-7.45 (t, 1H), 7.39-7.30 (m, 2H), 7.29-7.20 (t, 2H), 7.19-7.09 (m, 4H), 4.85-4.75 (m, 1H), 4.49-4.45 (t, 2H), 3.51-3.49 (m, 2H), 3.30-3.10 (m, 4H), 2.30-2.10 (m, 4H). MS: m/z=464.3 (M+1), HPLC: 95.43% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-eab422a288b34344b1340141a62740ea
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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