Benzaldehyde → tert-butyl 4-[4-[1-[(E)-benzylideneamino]pyrrolo[3,2-b]pyridin-6-yl]pyrazol-1-yl]piperidine-1-carboxylate

HRID 1404610Notes

Reaction equation

HRID 1404610 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:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]4)[CH:15]=3)[CH:9]=2)[CH:4]=[CH:3]1.[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:30]1(/[CH:29]=[N:1]/[N:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:12]=[N:13][N:14]([CH:16]5[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]5)[CH:15]=4)[CH:9]=3)[CH:4]=[CH:3]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 58532283tert-butyl 4-[4-(1-amino-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Product 1

HCID 58532304tert-butyl 4-[4-[1-[(E)-benzylideneamino]pyrrolo[3,2-b]pyridin-6-yl]pyrazol-1-yl]piperidine-1-carboxylateYield 81%

Conditions

Temperature
60 °C

Procedure

A mixture of tert-butyl 4-[4-(1-amino-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (30 mg, 0.078 mmol) and benzaldehyde (2.0 mL, excess) was heated to 60° C. for 10 min. Heptanes (4.0 ml) was added and the mixture was heated to reflux for 10 min. The product was purified by column chromatography (EtOAc:MeOH=100:5) and the entitled intermediate was isolated as a white solid (30 mg, 81% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 10 min
  3. customThe product was purified by column chromatography (EtOAc:MeOH=100:5)

Sources & evidence

ORD record
ord-3121fc37c0dd4e8aba7074080af75f0a
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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