tert-butyl 4-(2-amino-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate → 5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl) aniline

HRID 531681Notes

Reaction equation

HRID 531681 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=5)[CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[N:30]1[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]1>Cl.CCOCC.CO>[F:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[CH2:22][N:20]1[CH:21]=[C:17]([C:16]2[C:10]3[C:11](=[N:12][CH:13]=[C:8]([C:6]4[CH:5]=[CH:4][C:3]([N:30]5[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]5)=[C:2]([CH:7]=4)[NH2:1])[CH:9]=3)[NH:14][CH:15]=2)[CH:18]=[N:19]1

Participants

4

Reactant 1

HCID 90030996tert-butyl 4-(2-amino-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 729444255-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(piperazin-1-yl) anilineYield 7.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(2-amino-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (90 mg, 0.15 mmol) was deprotected in HCl in ether/MeOH (0.2/5 ml). This afforded 5 mg (6.3% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 9.00 (s, 1H), 8.70 (s, 1H), 8.40 (s, 1H), 8.06 (s, 1H), 7.98 (s, 1H), 7.90-7.80 (m, 2H), 7.63-7.61 (d, 1H), 7.45-7.35 (q, 1H), 7.20-7.00 (m, 3H), 5.45 (s, 2H), 3.12 (s, 2H), 2.76 (s, 4H). MS: m/z=467.9 (M+1), HPLC: 95.53% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-169b991dc9db4982a5576817ce3f1293
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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