Dimethylformamide → HCID 66703798, compound

HRID 426013Notes

Reaction equation

HRID 426013 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=O)C.[Cl:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[C:33]([NH:40][C@@H:41]2[CH2:46][CH2:45][CH2:44][CH2:43][C@H:42]2[N:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)[CH:32]=1.[NH2:53][C:54]1[CH:63]=[C:62]2[C:57]([CH2:58][CH2:59][C:60](=[O:65])[N:61]2[CH3:64])=[CH:56][CH:55]=1>O>[ClH:30].[Cl:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:53][C:54]2[CH:63]=[C:62]3[C:57]([CH2:58][CH2:59][C:60](=[O:65])[N:61]3[CH3:64])=[CH:56][CH:55]=2)=[O:36])=[C:33]([NH:40][C@@H:41]2[CH2:46][CH2:45][CH2:44][CH2:43][C@H:42]2[N:47]2[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]2)[CH:32]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 336993947-amino-1-methyl-3,4-dihydroquinolin-2(1H)-oneHCID 66703933HCID 66703933, compound

Product 1

HCID 66703798HCID 66703798, compoundYield 114.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

HATU (406 mg) was added to a DMF solution of 4-chloro-2-{[(1R,2R)-2-piperidin-1-ylcyclohexyl]amino}benzoic acid (300 mg) and 7-amino-1-methyl-3,4-dihydroquinolin-2(1H)-one (173 mg), followed by stirring at room temperature for 24 hours. After adding water to the reaction liquid and extracting with ethyl acetate, the organic layer was dried with sodium sulfate, and then the solution was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1). By treating the resulting free base with 4 M hydrogen chloride/ethyl acetate, 4-chloro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-{[(1R,2R)-2-piperidin-1-ylcyclohexyl]amino}benzamide hydrochloride (270 mg) was obtained as an amorphous.

Workup

  1. customto the reaction liquid
  2. extractionextracting with ethyl acetate
  3. dry with materialthe organic layer was dried with sodium sulfate
  4. concentrationthe solution was concentrated under a reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1)
  6. additionBy treating the resulting free base with 4 M hydrogen chloride/ethyl acetate

Sources & evidence

ORD record
ord-25a699e0d67d4ca28e0a1e7f7b3a0776
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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