1,1-Dichloroethane → HCID 66703839, compound

HRID 426012Notes

Reaction equation

HRID 426012 reaction equation
CN(C([O:8]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.ClC(Cl)C.[C:29]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([NH:42][C@H:43]2[CH2:48][CH2:47][CH2:46][CH2:45][C@@H:44]2[N:49]2[CH2:53][CH2:52][CH2:51][CH2:50]2)[CH:34]=1)([CH3:32])([CH3:31])[CH3:30].[NH2:54][C:55]1[CH:64]=[C:63]2[C:58]([CH2:59][CH2:60][C:61](=[O:66])[N:62]2[CH3:65])=[CH:57][CH:56]=1.[OH-:67].[Na+]>C(N(CC)CC)C>[C:37]([OH:39])(=[O:38])/[CH:36]=[CH:35]/[C:34]([OH:8])=[O:67].[C:29]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:54][C:55]2[CH:64]=[C:63]3[C:58]([CH2:59][CH2:60][C:61](=[O:66])[N:62]3[CH3:65])=[CH:57][CH:56]=2)=[O:38])=[C:35]([NH:42][C@H:43]2[CH2:48][CH2:47][CH2:46][CH2:45][C@@H:44]2[N:49]2[CH2:50][CH2:51][CH2:52][CH2:53]2)[CH:34]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

7

Reactant 5

HCID 63651,1-DichloroethaneHCID 14798Sodium HydroxideHCID 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 66703628HCID 66703628, compound

Product 1

HCID 66703839HCID 66703839, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

HATU (220 mg) and triethylamine (0.08 mL) were added to a dichloroethane (10 mL) solution of 4-tert-butyl-2-{[(1S,2S)-2-pyrrolidin-1-ylcyclohexyl]amino}benzoic acid (200 mg) and 7-amino-1-methyl-3,4-dihydroquinolin-2(1H)-one (102 mg), followed by stirring at room temperature for 12 hours. A 1 M sodium hydroxide aqueous solution was added to the reaction liquid, followed by extraction with chloroform. After drying of the organic layer, the solution was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform:methanol, 95:5). By adding fumaric acid (22 mg) to an ethyl acetate solution of the resulting free base, 4-tert-butyl-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-{[(1S,2S)-2-pyrrolidin-1-ylcyclohexyl]amino}benzamide fumarate (190 mg) was obtained as a solid.

Workup

  1. extractionfollowed by extraction with chloroform
  2. customAfter drying of the organic layer
  3. concentrationthe solution was concentrated under a reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol, 95:5)
  5. additionBy adding fumaric acid (22 mg) to an ethyl acetate solution of the resulting free base

Sources & evidence

ORD record
ord-1522f7c5049f4afd8a99b834256b9ffd
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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