1-(2,6-Dichloro-3-fluorophenyl)ethanone → N-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridin-1-amine

HRID 1404618Notes

Reaction equation

HRID 1404618 reaction equation
[NH2:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]4)[CH:15]=3)[CH:9]=2)[CH:4]=[CH:3]1.[Cl:29][C:30]1[C:35]([F:36])=[CH:34][CH:33]=[C:32]([Cl:37])[C:31]=1[C:38](=O)[CH3:39]>>[Cl:29][C:30]1[C:35]([F:36])=[CH:34][CH:33]=[C:32]([Cl:37])[C:31]=1[CH:38]([NH:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[CH:15]=3)[CH:9]=2)[CH:4]=[CH:3]1)[CH3:39]

Participants

3

Reactant 2

HCID 27339821-(2,6-Dichloro-3-fluorophenyl)ethanoneHCID 58532283tert-butyl 4-[4-(1-amino-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Product 1

HCID 58532258N-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridin-1-amine

Procedure

The entitled compound was prepared as described in example 27 by condensing tert-butyl 4-[4-(1-amino-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (prepared in example 18:100 mg, 0.26 mmol) with 1-(2,6-dichloro-3-fluorophenyl)ethanone (excess). The reduction of imine and BOC-deprotection were also carried out as described in Example 27.

Workup

  1. customThe entitled compound was prepared

Sources & evidence

ORD record
ord-d5aa360da4134ef0a36ac7ffd622bc35
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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