HCID 86600365, compound → HCID 90031477, compound

HRID 531559Notes

Reaction equation

HRID 531559 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)=[CH:18][CH:17]=4)[CH:14]=3)[NH:9][CH:8]=2)=[C:5]([CH3:35])[N:4]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[CH:38]=2)[N:3]=1.CO.[ClH:46].O1CCOCC1>>[ClH:46].[CH3:1][C:2]1[C:6]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:16]4[CH:17]=[CH:18][C:19]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:20][CH:21]=4)[CH:14]=3)[NH:9][CH:8]=2)=[C:5]([CH3:35])[N:4]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[CH:38]=2)[N:3]=1

Participants

3

Reactant 2

HCID 86600365HCID 86600365, compoundHCID 118523986HCID 118523986, compound

Product 1

HCID 90031477HCID 90031477, compoundYield 63%

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(4-(3-(3,5-dimethyl-1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (20 mg, 0.034 mmol) was deprotected in methanol/1,4-dioxane HCl in (0.3/1 ml). This afforded 10 mg (63% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.74 (s, 1H), 8.65 (s, 1H), 7.86 (s, 1H), 7.71-7.69 (d, 2H), 7.32-7.29 (t, 1H), 7.20-7.15 (m, 4H), 7.09-7.07 (d, 1H), 5.51 (s, 2H), 3.53-3.50 (m, 4H), 3.41-3.38 (m, 4H), 2.36-2.34 (m, 9H). MS: m/z=477.2 (M+1) HPLC 98.14% (method B).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-9ce4c82c8f5b4a4b8e5912b7e57eff91
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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