HCID 118523943, compound → HCID 90030600, compound

HRID 531661Notes

Reaction equation

HRID 531661 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)[CH2:26][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]([CH2:26][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:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 118523943HCID 118523943, compound

Product 1

HCID 90030600HCID 90030600, compoundYield 40.9%

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)benzyl)piperidine-1-carboxylate (60 mg, 0.106 mmol) was deprotected in HCl in methanol (5 ml). This afforded 20 mg (32.4% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.65-8.60 (bs, 1H), 8.52 (s, 1H), 7.92 (s, 1H), 7.87 (s, 1H), 7.74 (s, 1H), 7.61-7.58 (d, 2H), 7.53-7.41 (t, 1H), 7.33-7.26 (d, 1H), 7.26-7.22 (t, 2H), 7.15-7.09 (m, 3H), 4.49-4.45 (t, 2H), 3.41-3.38 (d, 2H), 3.22-3.18 (t, 2H), 2.99-2.93 (t, 2H), 2.77-2.76 (d, 2H), 2.01-1.90 (m, 3H), 1.56-1.46 (m, 2H). MS: m/z=462.7 (M+1), HPLC: 88.14% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-ab4f3caab7c544a6a6c26aeed3888a5d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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