HCID 90031554, compound → HCID 90030544, compound

HRID 531552Notes

Reaction equation

HRID 531552 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][CH:43]=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]=[CH:25][C:24]([N:27]5[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]5)=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:40])=[N:7]1>CO.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][CH:43]=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]=[CH:23][C:24]([N:27]5[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]5)=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:40])=[N:7]1

Participants

3

Reactant 1

HCID 90031554HCID 90031554, compound

Product 1

HCID 90030544HCID 90030544, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(4-(3-(1-(3-chlorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (12 mg, 0.02 mmol) was deprotected in methanol/1,4-dioxane in (0.3/2 ml). This afforded 5 mg (55% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.72 (s, 1H), 8.669 (s, 1H), 7.85 (s, 1H), 7.71-7.69 (d, 2H), 7.42-7.39 (m, 2H), 7.32 (s, 1H), 7.24-7.18 (m, 3H), 5.52 (s, 2H), 3.53-3.50 (m, 4H), 3.41-3.38 (m, 4H), 2.33-2.32 (d, 6H). MS: m/z=497.2 (M+1), HPLC—95.77% (method-B).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-002d42a069654e67a03b41c8a9d75b57
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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