HCID 131735673, compound → HCID 72944534, compound

HRID 531652Notes

Reaction equation

HRID 531652 reaction equation
N1(C(O[NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH:18]=[C:19]4[C:25]([C:26]5[C:27]([CH3:40])=[N:28][N:29]([CH2:32][C:33]6[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=6)[C:30]=5[CH3:31])=[CH:24][NH:23][C:20]4=[N:21][CH:22]=3)[CH:12]=2)=O)CCCCC1>Cl.CO>[F:39][C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[CH2:32][N:29]1[C:30]([CH3:31])=[C:26]([C:25]2[C:19]3[C:20](=[N:21][CH:22]=[C:17]([C:13]4[CH:12]=[C:11]([NH:10][CH:18]5[CH2:17][CH2:22][NH:21][CH2:20][CH2:19]5)[CH:16]=[CH:15][CH:14]=4)[CH:18]=3)[NH:23][CH:24]=2)[C:27]([CH3:40])=[N:28]1

Participants

4

Reactant 1

HCID 131735673HCID 131735673, compound

Product 1

HCID 72944534HCID 72944534, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-((3-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)amino piperidine-1-carboxylate (80 mg, 0.134 mmol) was deprotected in HCl in methanol (5 ml). This afforded 16 mg (20.4% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.8-8.6 (bs, 1H), 8.37 (s, 1H), 7.67 (s, 1H), 7.41-7.35 (m, 2H), 7.12-7.10 (m, 2H), 7.06-7.04 (m, 2H), 6.94-6.90 (m, 2H), 5.41 (s, 2H), 3.85-3.70 (m, 1H), 3.50-3.47 (m, 2H), 3.18-3.12 (t, 2H), 2.29-2.24 (m, 8H), 1.79-1.76 (m, 2H). MS: m/z=495.3 (M+1), HPLC: 85.03% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-84457c83edb3486cb7c526734b13d577
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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