Potassium Carbonate → 1,1-dimethylethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]propanoate

HRID 1514188노트

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HRID 1514188 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:27]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:27]4[CH2:26][CH2:25][N:24]([CH2:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:23][CH2:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 256128tert-Butyl 3-bromopropionateHCID 441287466-(5-{3-chloro-4-[(1-methyl ethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine

생성물 1

HCID 594034501,1-dimethylethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]propanoate수율 25.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

In a 5 ml microwave reaction vessel was added 6-(5-{3-chloro-4-[(1-methyl ethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine (Free base of Example 8, obtained by standard methods e.g. partitioning between organic and basic aqueous solvents and collecting organic solvent) (70 mg) in DMF (3 ml) to give a brown solution. Then potassium carbonate (101 mg) was added followed by 1,1-dimethylethyl 3-bromopropanoate (38.1 mg, 0.182 mmol). The reaction mixture was heated at 100° C. for 10 minutes. The cooled reaction mixture was diluted with DCM (5 ml) and purified by SCX (washing with methanol and eluting the crude amino ester with methanolic ammonia). Purification by MDAP yielded the amino ester, 1,1-dimethylethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]propanoate (25 mg, 0.046 mmol, 25.4% yield) isolated as a light yellow oil. MS (ES) C28H3435ClN3O4 requires 511; found 512 [M+H]+.

후처리

  1. customobtained by standard methods e.g.
  2. custompartitioning between organic and basic aqueous solvents
  3. customcollecting organic solvent) (70 mg) in DMF (3 ml)
  4. customto give a brown solution
  5. customThe cooled reaction mixture
  6. custompurified by SCX (
  7. washwashing with methanol
  8. washeluting the crude amino ester with methanolic ammonia)
  9. customPurification by MDAP

출처 및 근거

ORD 기록
ord-10727254f4f045459d5b06f65937bce0
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222245B2

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