HCID 90033731, compound → HCID 90031293, compound

HRID 531857Notes

Reaction equation

HRID 531857 reaction equation
[F:1][C:2]1[C:3]([N:30]2[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]2)=[N:4][CH:5]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=5)[CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:7]=1>CO.Cl.CCOCC>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=5)[CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[N:4][C:3]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1

Participants

4

Reactant 1

HCID 90033731HCID 90033731, compound

Product 1

HCID 90031293HCID 90031293, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(3-fluoro-5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate (125 mg, 0.218 mmol) was deprotected in methanol/HCl in ether (5/2.5 ml) to afford 72 mg (56.2% yield) of the titled compound after purification by prep HPLC. 1H NMR (CD3OD, 300 MHz): δ 8.646-8.640 (d, 1H), 8.56 (s, 1H), 8.419-8.415 (d, 1H), 8.28 (s, 1H), 7.97 (s, 1H), 7.94-7.93 (d, 1H), 7.77 (s, 1H), 7.36-7.33 (m, 1H), 7.11-6.98 (m, 3H), 5.42 (s, 2H), 3.80-3.77 (m, 4H), 3.40-3.31 (m, 4H). MS: m/z=472.3 (M+1), HPLC: 98.87% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-8d178542fc4c41b185946787f9a4254d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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