HCID 118524089, compound → HCID 90030108, compound

HRID 531816Notes

Reaction equation

HRID 531816 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][CH:41]=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]=[CH:22][C:23]([CH: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:39]=[CH:40][CH:41]=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]([CH:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[CH:22][CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 1

HCID 118524089HCID 118524089, compound

Product 1

HCID 90030108HCID 90030108, compoundYield 63%

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)pyridin-2-yl)piperidine-1-carboxylate (96 mg, 0.173 mmol) was deprotected in methanol/HCl in dioxane (5/5 ml) to afford 49 mg (63% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 9.178-9.170 (d, 1H), 8.78-8.74 (dd, 1H), 8.71-8.66 (dd, 2H), 8.26 (s, 1H), 7.99 (s, 1H), 7.95-7.92 (d, 1H), 7.77 (s, 1H), 7.40-7.31 (q, 1H), 7.10-7.08 (d, 1H), 7.03-6.96 (m, 2H), 5.42 (s, 2H), 3.63-3.59 (d, 2H), 3.55-3.40 (m, 1H), 3.30-3.19 (m, 2H), 2.32-2.08 (m, 4H). MS: m/z=453.5 (M+1), HPLC: 93.40% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-99784ea7abe74fc99efb44d27f0790f9
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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