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

HRID 531641Notes

Reaction equation

HRID 531641 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[N:17][CH:18]=[C:19]([C:22]5[CH:27]=[CH:26][C:25]([CH:28]6[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]6)=[CH:24][CH:23]=5)[CH:20]=4)[NH:15][CH:14]=3)[CH:10]=[N:9]2)[CH:2]=1>C(O)(C(F)(F)F)=O.CO>[NH:31]1[CH2:32][CH2:33][CH:28]([C:25]2[CH:26]=[CH:27][C:22]([C:19]3[CH:20]=[C:21]4[C:13]([C:11]5[CH:10]=[N:9][N:8]([CH2:7][C:3]6[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=6)[CH:12]=5)=[CH:14][NH:15][C:16]4=[N:17][CH:18]=3)=[CH:23][CH:24]=2)[CH2:29][CH2:30]1

Participants

3

Reactant 1

HCID 118524104tert-butyl 4-(4-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 729443295-(4-(piperidin-4-yl)phenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 15.4%

Reagents, catalysts & solvents 1

HCID 86669916Methanol trifluoroacetic acidSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(4-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (120 mg, 0.224 mmol) was deprotected in TFA/methanol (5/5 ml). This afforded 15 mg (12% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.76 (s, 2H), 8.56-8.55 (d, 2H), 8.36-8.34 (m, 2H), 8.02 (s, 1H), 7.95-7.91 (m, 1H), 7.75-7.72 (m, 3H), 7.45-7.42 (m, 2H), 5.66 (s, 2H), 3.56-3.51 (d, 2H), 3.22-3.14 (t, 2H), 3.10-2.99 (m, 1H), 2.16-2.11 (d, 2H), 2.03-1.93 (td, 2H). MS: m/z=435.2 (M+1), HPLC: 97.0% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-b8bb767094a24bce970abecc248360d3
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…