1,3-Dimethyl-2-imidazolidinone → HCID 67277927, compound

HRID 1696231Notes

Reaction equation

HRID 1696231 reaction equation
Cl[C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=[C:4]2[NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:13][C:3]=12.Cl.[CH3:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]1[NH2:29].C(N(CC)C(C)C)(C)C.CN1CCN(C)C1=O>CCOC(C)=O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[NH:11][C:4]3=[N:5][CH:6]=[C:7]([C:8]([NH2:10])=[O:9])[C:2]([NH:29][C@H:24]4[CH2:25][CH2:26][CH2:27][CH2:28][C@H:23]4[CH3:22])=[C:3]3[CH:13]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 81531DiisopropylethylamineHCID 119839064-Chloro-2-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamideHCID 67278079(1S,2R)-2-methylcyclohexanamine hydrochloride

Product 1

HCID 67277927HCID 67277927, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-2-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (70 mg),(1S,2R)-2-methylcyclohexanamine hydrochloride (108.5 mg),N,N-diisopropylethylamine (0.126 ml) and 1,3-dimethyl-2-imidazolidinone (0.35 ml) were combined and irradiated microwave at 16° C. for 1 hour. After cooled to ambient temperature, the mixture was diluted in EtOAc. The organic solution was washed with saturated aqueous sodium hydrogencarbonate, dried over MgSO4 and evaporated in vacuo. The residue was purified by preparative NH2 silica gel column chromatography with 5% methanol in chloroform to give 2-(4-fluorophenyl)-4-{[(1S,2R)-2-methylcyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (13.7 mg) as an off-white solid.

Workup

  1. customirradiated microwave at 16° C. for 1 hour
  2. washThe organic solution was washed with saturated aqueous sodium hydrogencarbonate
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative NH2 silica gel column chromatography with 5% methanol in chloroform

Sources & evidence

ORD record
ord-287af73f70f647a7a0f9a8102448cc02
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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