HCID 90030036, compound → HCID 90031561, compound

HRID 531649Notes

Reaction equation

HRID 531649 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]([CH:28]5[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]5)=[CH:24][CH:23]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH:10]=[N:9]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:31]1[CH2:32][CH2:33][CH:28]([C:25]2[CH:24]=[CH:23][C:22]([C:19]3[CH:20]=[C:21]4[C:13]([C:11]5[CH:10]=[N:9][N:8]([CH2:7][C:2]6[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=6)[CH:12]=5)=[CH:14][NH:15][C:16]4=[N:17][CH:18]=3)=[CH:27][CH:26]=2)[CH2:29][CH2:30]1

Participants

3

Reactant 1

HCID 90030036HCID 90030036, compound

Product 1

HCID 90031561HCID 90031561, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(4-(3-(1-(pyridin-2-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (110 mg, 0.205 mmol) was deprotected in TFA/DCM (5/5 ml). This afforded 10 mg (11.1% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.73 (s, 1H), 8.68-8.67 (d, 1H), 8.59 (s, 1H), 8.38 (s, 1H), 8.16-8.11 (t, 1H), 8.01 (s, 1H), 7.81 (s, 1H), 7.75-7.72 (d, 2H), 7.66-7.61 (t, 1H), 7.49-7.42 (m, 3H), 5.68 (s, 2H), 3.55-3.51 (d, 2H), 3.21-3.13 (m, 2H), 3.03-2.95 (m, 1H), 2.14-1.90 (m, 4H). MS: m/z=434.9 (M+1), HPLC: 92.12% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-5b535e4173724c0fa8621dd6558efd0b
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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