4-Methylmorpholine → HCID 74222630、化合物

HRID 1624139

反応式

HRID 1624139 の反応式
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([O:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][C:7]([CH3:16])=[CH:6][N:5]2[C:17]=1[C:18]([OH:20])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[NH2:50][C@H:51]([CH2:54][CH2:55][CH2:56][CH3:57])[CH2:52][OH:53]>CN(C=O)C.O.C(O)(C(F)(F)F)=O>[OH:53][CH2:52][C@H:51]([NH:50][C:18]([C:17]1[N:5]2[CH:6]=[C:7]([CH3:16])[CH:8]=[C:9]([O:10][CH2:11][CH2:12][CH:13]([CH3:14])[CH3:15])[C:4]2=[N:3][C:2]=1[CH3:1])=[O:20])[CH2:54][CH2:55][CH2:56][CH3:57]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6994402(R)-2-Aminohexan-1-olHCID 86717930HCID 86717930、化合物

生成物 1

HCID 74222630HCID 74222630、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 22392675Trifluoroacetic acid water溶媒

実験手順

75 mg (0.27 mmol) of 2,6-dimethyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxylic acid Example 89A, 96 mg (0.30 mmol) of TBTU and 110 mg (1.09 mmol) of 4-methylmorpholine were initially charged in 1.73 ml of DMF. 35 mg (0.30 mmol) of (R)-(−)-2-aminohexanol were then added, and the mixture was stirred at room temperature overnight. The reaction solution was diluted with water/TFA and purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). The concentrated fractions were taken up in dichloromethane and washed twice with saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted two more times with dichloromethane, the combined organic phases were dried over sodium sulphate and filtered and the filtrate was concentrated and lyophilized. This gave 91 mg of the target compound (87.5% of theory, purity 98%).

後処理

  1. custompurified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA)
  2. washwashed twice with saturated aqueous sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted two more times with dichloromethane
  4. dry with materialthe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-db640b64780a4ee5baf970f15c0fb0df
出典データセット
uspto-grants-2014_07
特許番号
US08778964B2

関連ノート

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