Hydrochloric Acid → 5-(4-(piperazin-1-yl)phenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 531750Notes

Reaction equation

HRID 531750 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]([N: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.Cl>CCOCC.CO>[N:28]1([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][NH:31][CH2:32][CH2:33]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118524047tert-butyl 4-(4-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 900305005-(4-(piperazin-1-yl)phenyl)-3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 11.1%

Reagents, catalysts & solvents 1

HCID 21864698Diethyl ether methanolSolvent

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)piperazine-1-carboxylate (100 mg, 0.186 mmol) was deprotected with HCl in ether/methanol (2/3 ml). This afforded 9 mg (11.0% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.54 (s, 1H), 8.34-8.28 (d, 1H), 8.50-8.49 (d, 1H), 8.43-8.42 (d, 1H), 8.307-8.300 (d, 1H), 8.23 (s, 1H), 7.93 (s, 1H), 7.79-7.77 (d, 1H), 7.64-7.61 (m, 3H), 7.45-7.41 (m, 1H), 7.14-7.11 (m, 2H), 5.49 (s, 2H), 3.38-3.31 (m, 4H), 3.30-3.23 (m, 4H). MS: m/z=436.2 (M+1), HPLC: 97.13% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-9bd84cf2cbbf4f168ed57e70aeab0b90
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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