4-Methylmorpholine → HCID 90114467, 화합물

HRID 2275900노트

반응식

HRID 2275900 반응식
Cl.[F:2][C:3]([F:10])([F:9])[C:4]([CH3:8])([NH2:7])[CH2:5][NH2:6].[F:11][C:12]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:13]=1[CH2:14][O:15][C:16]1[C:17]2[N:18]([C:23]([C:27](O)=[O:28])=[C:24]([CH3:26])[N:25]=2)[CH:19]=[C:20]([CH3:22])[CH:21]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>CN(C=O)C.O.C(O)(C(F)(F)F)=O>[NH2:7][C:4]([CH3:8])([C:3]([F:10])([F:9])[F:2])[CH2:5][NH:6][C:27]([C:23]1[N:18]2[CH:19]=[C:20]([CH3:22])[CH:21]=[C:16]([O:15][CH2:14][C:13]3[C:30]([F:34])=[CH:31][CH:32]=[CH:33][C:12]=3[F:11])[C:17]2=[N:25][C:24]=1[CH3:26])=[O:28]

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 73236151HCID 73236151, 화합물2회HCID 867178848-[(2,6-Difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid

생성물 1

HCID 90114467HCID 90114467, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 22392675Trifluoroacetic acid water용매

실험 절차

118 mg (0.66 mmol) of rac-3,3,3-trifluoro-2-methylpropane-1,2-diamine hydrochloride Example 246A were added to 200 mg (0.60 mmol) of 8-[(2,6-difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid Example 21A, 203 mg (0.63 mmol) of TBTU and 0.27 ml (2.41 mmol) of 4-methylmorpholine in DMF (2.1 ml), and the reaction mixture was stirred at RT overnight. 50 mg (0.28 mmol) of rac-3,3,3-trifluoro-2-methylpropane-1,2-diamine hydrochloride Example 246A were added to the reaction mixture, and stirring was continued at RT overnight. The mixture was diluted with water/TFA and purified by preparative RP-HPLC (acetonitrile/water gradient with addition of 0.1% TFA). The product fraction was concentrated. Saturated aqueous sodium bicarbonate solution was added to the residue, and the mixture was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered off and concentrated. This gave 219 mg (79% of theory, purity 99%) of the target compound.

후처리

  1. stirringstirring
  2. waitwas continued at RT overnight
  3. custompurified by preparative RP-HPLC (acetonitrile/water gradient with addition of 0.1% TFA)
  4. concentrationThe product fraction was concentrated
  5. additionSaturated aqueous sodium bicarbonate solution was added to the residue
  6. extractionthe mixture was extracted three times with dichloromethane
  7. dry with materialThe combined organic phases were dried over sodium sulphate
  8. filtrationfiltered off
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3213b702de0141ecbcf0049fa7781cf8
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126998B2

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