Triethylamine → HCID 11647739, compound

HRID 225800Notes

Reaction equation

HRID 225800 reaction equation
C(OP(C#N)(=O)OCC)C.C(N(CC)CC)C.Cl.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([CH3:28])=[N:25][C:24]=2[CH:29]=1.[F:30][C:31]([F:51])([F:50])[C:32]1[CH:33]=[C:34]([N:38]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[C:39]2[C:47](O)=[O:48])[CH:35]=[CH:36][CH:37]=1>CN(C)C=O>[CH3:28][C:26]1[O:27][C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:47]([C:39]3[N:38]([C:34]4[CH:35]=[CH:36][CH:37]=[C:32]([C:31]([F:51])([F:30])[F:50])[CH:33]=4)[C:46]4[C:41]([CH:40]=3)=[CH:42][CH:43]=[CH:44][CH:45]=4)=[O:48])=[CH:29][C:24]=2[N:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 574403182-Methyl-1,3-benzoxazol-5-amine--hydrogen chloride (1/1)HCID 574403191-[3-(Trifluoromethyl)phenyl]-1H-indole-2-carboxylic acid

Product 1

HCID 11647739HCID 11647739, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.091 ml (0.6 mmol) of diethylcyanophosphonate, 0.168 ml (0.6 mmol) of triethylamine and 0.111 g (0.6 mmol) of 5-amino-2-methylbenzoxazole hydrochloride are added to a solution of 0.152 g (0.5 mmol) of 1-[3-(trifluoromethyl)phenyl]-1H-indole-2-carboxylic acid (JP2001151771A2) in 3 ml of dimethylformamide. The mixture is stirred overnight at room temperature and concentrated under reduced pressure, and the residue is taken up in water and dichloromethane. After separation of the phases by settling, the organic phase is dried and evaporated under reduced pressure. The residue is purified by preparative chromatography. 0.102 g of solid is obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customAfter separation of the phases
  3. customthe organic phase is dried
  4. customevaporated under reduced pressure
  5. customThe residue is purified by preparative chromatography

Sources & evidence

ORD record
ord-116f969d737b4594a50357935f48efd6
Source dataset
uspto-grants-2009_07
Patent number
US07557134B2

Reaction notes

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