3-Methoxyaniline → HCID 57840939, compound

HRID 733697Notes

Reaction equation

HRID 733697 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.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32]>C(OCC)C>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([NH:32][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:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 108243-MethoxyanilineHCID 578409911,1-Dimethylethyl 7-chloro-3-methyl-4-(1-piperidinylcarbonyl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Product 1

HCID 57840939HCID 57840939, 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-methoxyaniline (54 ul) instead of 3-bromoaniline and heating for 15 rather than 30 minutes. Isolated by MDAP rather than trituration with diethyl ether to give 1-[7-(3-methoxy-phenylamino)-3-methyl-1H-pyrrolo[2,3-c]pyridin-4-yl]-1-piperidin-1-yl-methanone (65 mg).

Workup

  1. temperatureheating for 15 rather than 30 minutes

Sources & evidence

ORD record
ord-7f43ed7d561147d9bfa3a24f23d604b8
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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