3-Chloroaniline → HCID 68869691, compound

HRID 733702Notes

Reaction equation

CC(OC([N:8]1[C:12]2=[C:13]([Cl:28])[N:14]=[CH:15][C:16]([C:17](=[O:27])[N:18]([CH3:26])[CH2:19][CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[C:11]2[C:10]([CH3:29])=[CH:9]1)=O)(C)C.[Cl:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34]>>[ClH:28].[CH3:26][N:18]([CH2:19][CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:17]([C:16]1[C:11]2[C:10]([CH3:29])=[CH:9][NH:8][C:12]=2[C:13]([NH:34][C:33]2[CH:35]=[CH:36][CH:37]=[C:31]([Cl:30])[CH:32]=2)=[N:14][CH:15]=1)=[O:27]

Participants

Reactant 2

HCID 79323-Chloroaniline

HCID 57841026HCID 57841026, compound

Product 1

HCID 68869691HCID 68869691, compound

Procedure

Prepared in a similar manner to Example 4(d) from 7-chloro-3-methyl-4-[methyl-(tetrahydro-pyran-4-ylmethyl)-carbamoyl]-pyrrolo[2,3-c]pyridine-1-carboxylic acid dimethyl-ethyl ester (120 mg) and 3-chloroaniline instead of 3-bromoaniline. Purified by Biotage chromatography over silica gel eluting with ethyl acetate rather than trituration with diethyl ether. The salt formation was as Example 4 (d) to afford the title compound (70 mg).

Workup

customPurified by Biotage chromatography over silica gel eluting with ethyl acetate rather than trituration with diethyl ether

Sources & evidence

ORD record: ord-44ce6d8773034bca9c432aa8ff7bff05
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589206B2

Reaction notes

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