4-Methylmorpholine → HCID 86603052, 화합물

HRID 855348노트

반응식

HRID 855348 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:14]([C:18]1[CH:37]=[CH:36][C:21]([CH2:22][NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[C:14]([C:18]1[CH:37]=[CH:36][C:21]([CH2:22][N:23]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[CH:27]=2)[C:11]([C:9]2[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]3[C:8]=2[NH:7][CH:6]=[CH:5]3)=[O:13])=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 533992575-Bromo-1H-indole-7-carboxylic acidHCID 68560440(4-Tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

생성물 1

HCID 86603052HCID 86603052, 화합물수율 90.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 80 mg (0.3 mmol) 5-bromo-1H-indole-7-carboxylic acid and 112 mg (0.33 mmol) (4-tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine in 3 ml DMF, were added 0.1 ml (0.91 mmol) of N-methylmorpholine and 173 mg of TBTU (0.45 mmol) at rt. After stirring for 17 h at rt, the reaction mixture was diluted with 33 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; DCM/heptane 50:50 to 70:30) to give 152 mg white powder (90%). MS (ISP) 574.3 (M+H)+.

후처리

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (8 g silica gel; DCM/heptane 50:50 to 70:30)

출처 및 근거

ORD 기록
ord-1f53a45b2eda414ba82e446c03cc8d7e
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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