4-Methylmorpholine → HCID 90114467、化合物

HRID 2275900ノート

反応式

HRID 2275900 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 90114467HCID 90114467、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 22392675Trifluoroacetic acid water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3213b702de0141ecbcf0049fa7781cf8
出典データセット
uspto-grants-2015_09
特許番号
US09126998B2

反応ノート

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