3-Chloroaniline → HCID 44475668, compound

HRID 733694Notes

Reaction equation

HRID 733694 reaction equation
C(OC([N:8]1[C:12]2=[C:13](Cl)[N:14]=[CH:15][C:16]([C:17]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])=[C:11]2[C:10]([CH3:26])=[CH:9]1)=O)(C)(C)C.[Cl:27][C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=1)[NH2:31]>C(OCC)C>[Cl:27][C:28]1[CH:29]=[C:30]([NH:31][C:13]2[N:14]=[CH:15][C:16]([C:17]([N:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[O:18])=[C:11]3[C:10]([CH3:26])=[CH:9][NH:8][C:12]=23)[CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 578409911,1-Dimethylethyl 7-chloro-3-methyl-4-(1-piperidinylcarbonyl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Product 1

HCID 44475668HCID 44475668, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared in a similar manner to Example 4(d) from 7-chloro-3-methyl-4-(1-piperidin-1-yl-methanoyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester (90 mg) and using 3-chloroaniline (50 ul) instead of 3-bromoaniline and heating for 15 rather than 30 minutes. Isolated by MDAP rather than trituration with diethyl ether to give the title compound (67 mg).

Workup

  1. temperatureheating for 15 rather than 30 minutes

Sources & evidence

ORD record
ord-7f30ab89a871470189a2fbc9fad93cce
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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