HCID 118524103, compound → HCID 90031650, compound

HRID 531859Notes

Reaction equation

HRID 531859 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][CH:43]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[C:22]([O:39][CH3:40])[C:23]([N:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)=[N:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1>CO.Cl.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][CH:43]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[N:24][C:23]([N:26]5[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]5)=[C:22]([O:39][CH3:40])[CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 1

HCID 118524103HCID 118524103, compound

Product 1

HCID 90031650HCID 90031650, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-yl)piperazine-1-carboxylate (91 mg, 0.156 mmol) was deprotected in methanol/HCl in dioxane (5/5 ml) to afford 52 mg (56% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.727-8.722 (d, 1H), 8.626-8.622 (d, 1H), 8.29 (s, 1H), 8.19-8.18 (d, 1H), 8.00 (s, 1H), 7.81 (s, 1H), 7.75-7.74 (d, 1H), 7.37-7.35 (q, 1H), 7.12-7.10 (d, 1H), 7.02-6.99 (m, 2H), 5.44 (s, 2H), 4.03 (s, 3H), 3.78-3.74 (t, 4H), 3.39-3.32 (m, 4H). MS: m/z=484.3 (M+1), HPLC: 97.58% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-da6da193fdd24d8f9bdb3a92cde50c67
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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