Pyridine → HCID 178487950, compound

HRID 245724Notes

Reaction equation

HRID 245724 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[N:12]3[CH:13]=[CH:14][N:15]=[C:16]([CH3:17])[C:11]3=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]4[N:28]([CH3:38])[C:29]5[C:34]([CH:35]=4)=[C:33]([O:36][CH3:37])[CH:32]=[CH:31][CH:30]=5)=[O:26])=[C:20]([O:39][CH3:40])[CH:19]=3)[N:9]=2)[CH2:4][CH2:3]1.[CH:41]1([N:46]=[C:47]=[O:48])[CH2:45][CH2:44][CH2:43][CH2:42]1.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[CH:41]1([NH:46][C:47](=[O:48])[O:1][C@H:2]2[CH2:7][CH2:6][C@H:5]([C:8]3[N:12]4[CH:13]=[CH:14][N:15]=[C:16]([CH3:17])[C:11]4=[C:10]([C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]5[N:28]([CH3:38])[C:29]6[C:34]([CH:35]=5)=[C:33]([O:36][CH3:37])[CH:32]=[CH:31][CH:30]=6)=[O:26])=[C:20]([O:39][CH3:40])[CH:19]=4)[N:9]=3)[CH2:4][CH2:3]2)[CH2:45][CH2:44][CH2:43][CH2:42]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 643500Cyclopentyl IsocyanateHCID 178487948HCID 178487948, compound

Product 1

HCID 178487950HCID 178487950, compoundYield 24.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To N-(4-(3-((trans)-4-hydroxycyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide (0.037 mmol, 20 mg) and N,N-dimethylpyridin-4-amine (7.41 μmol, 0.906 mg) in dichloromethane (2 ml) was added cyclopentyl isocyanate (0.185 mmol, 20.60 mg) and the mixture was stirred at room temperature overnight. Then pyridine (2 ml) was added and the mixture was stirred overnight at 90° C. The reaction mixture was diluted with ethyl acetate and the obtained suspension was filtered. The filtrate was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 5% methanol) to give (trans)-4-(1-(3-methoxy-4-(4-methoxy-1-methyl-1H-indole-2-carboxamido)phenyl)-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl cyclopentylcarbamate (6 mg).

Workup

  1. stirringthe mixture was stirred overnight at 90° C
  2. filtrationthe obtained suspension was filtered
  3. customThe filtrate was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 5% methanol)

Sources & evidence

ORD record
ord-85fd7182d3cd428a94b8cef7f58f9fed
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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