Hydrochloric Acid → HCID 68867274, compound

HRID 733699Notes

Reaction equation

HRID 733699 reaction equation
C(OC([N:8]1[C:12]2=[C:13]([Cl:25])[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.[C:27]([C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32])#[N:28].C(OCC)C.Cl>C(OCC)(=O)C.C(OCC)C>[ClH:25].[C:27]([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)#[N:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 167023-AminobenzonitrileHCID 578409911,1-Dimethylethyl 7-chloro-3-methyl-4-(1-piperidinylcarbonyl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Product 1

HCID 68867274HCID 68867274, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherCatalystHCID 8857Ethyl AcetateSolvent

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-cyanoaniline (56 mg) instead of 3-bromoaniline and heating for 15 rather than 30 minutes. Isolated by MDAP rather than trituration with diethyl ether and then suspended in ethyl acetate (10 ml) and treated with a solution of 1M hydrochloric acid in diethyl ether (10 drops). The mixture was evaporated and dried at 40° C. under vacuum to afford the title compound (25 mg).

Workup

  1. temperatureheating for 15 rather than 30 minutes
  2. customThe mixture was evaporated
  3. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-e0938af2f7be48f78b4fbb910f327611
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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