tert-butyl 4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperidine-1-carboxylate → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-(piperidin-4-ylmethyl)phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 531670Notes

Reaction equation

HRID 531670 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[CH:41][CH:42]=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]([CH:37]=[CH:38][CH:39]=4)[CH2:23][CH:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1>CO.CCOCC.Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[CH:41][CH:42]=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:39]=[CH:38][CH:37]=[C:22]([CH2:23][CH:24]5[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]5)[CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

3

Reactant 1

HCID 90030772tert-butyl 4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperidine-1-carboxylate

Product 1

HCID 729444233-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-(piperidin-4-ylmethyl)phenyl)-1H-pyrrolo[2,3-b]pyridineYield 97.6%

Reagents, catalysts & solvents 1

HCID 131735674methanol ether HClSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzyl)piperidine-1-carboxylate (50 mg, 0.088 mmol) was deprotected in methanol/ether HCl (5/1 ml). This afforded 40 mg (90.9% yield) of the titled compound. 1H NMR (DMSO-d6, 300 MHz): δ 11.9 (s, 1H), 8.75-8.65 (bs, 1H), 8.53-8.52 (d, 1H), 8.42-8.38 (m, 2H), 7.98 (s, 1H), 7.78-7.77 (d, 2H), 7.62-7.57 (m, 2H), 7.43-7.35 (m, 2H), 7.19-7.05 (m, 4H), 5.40 (s, 2H), 3.23-3.18 (d, 2H), 2.80-2.54 (m, 5H), 2.25-2.15 (bs, 1H), 1.76-1.71 (d, 2H), 1.45-1.30 (m, 2H). MS: m/z=466.2 (M+1), HPLC: 97.04% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d9adc9e1f24449c59dc36c42335c30f8
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…