Trifluoroacetic acid methylene chloride → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 531752Notes

Reaction equation

HRID 531752 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:49]=[CH:50][CH:51]=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]=[CH:22][C:23]([N:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)=[N:24][CH:25]=4)[CH:18]=3)[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:12]=2)[CH:8]=[N:7]1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[F:1][C:2]1[CH:3]=[C:4]([CH:49]=[CH:50][CH:51]=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:25]=[N:24][C:23]([N:26]5[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]5)=[CH:22][CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 90031460tert-butyl 4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 900314653-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridineYield 30.6%

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate (70 mg, 0.126 mmol) was deprotected with TFA/DCM (1/5 ml). This afforded 17.5 mg (24.3% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.53 (s, 3H), 8.23 (s, 1H), 8.16-8.12 (dd, 1H), 7.97 (s, 1H), 7.73 (s, 1H), 7.40-7.30 (m, 1H), 7.20-7.10 (m, 2H), 7.09-6.95 (m, 1H), 5.43 (s, 2H), 3.92-2.89 (m, 4H), 3.40-3.36 (m, 4H). MS: m/z=464.2 (M+1), HPLC: 97.79% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-8786180f798a43a19925bf4953697445
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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