Triethylamine → Tert-butyl 4-(4-amino-3-fluorobenzoyl)-2,2-dimethylpiperazine-1-carboxylate

HRID 1878393노트

반응식

HRID 1878393 반응식
[CH3:1][C:2]1([CH3:15])[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[NH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][C:18]=1[F:26].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(OCC)(=O)C>[NH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([N:6]2[CH2:5][CH2:4][N:3]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:2]([CH3:15])([CH3:1])[CH2:7]2)=[O:22])=[CH:19][C:18]=1[F:26]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 299224001,1-Dimethylethyl 2,2-dimethyl-1-piperazinecarboxylate

생성물 1

HCID 66878622Tert-butyl 4-(4-amino-3-fluorobenzoyl)-2,2-dimethylpiperazine-1-carboxylate수율 83.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To tert-butyl 2,2-dimethylpiperazine-1-carboxylate (0.902 mmol, 0.193 g) in dichloro-methane (5 mL) was added 4-amino-3-fluorobenzoic acid (0.902 mmol, 0.14 g), and triethylamine (1.805 mmol, 0.252 mL, 0.183 g). To this mixture was added 1-propanephosphonic acid cyclic anhydride (1.805 mmol, 1.074 mL, 1.149 g, 50% solution in ethyl acetate). After 2 hours stirring, ethyl acetate was added and the organic mixture was washed with saturated sodium hydrogen carbonate, water, and saturated sodium chloride. The organic layer was dried with sodium sulfate, filtered and concentrated under vacuum to give the intermediate tert-butyl 4-(4-amino-3-fluorobenzoyl)-2,2-dimethylpiperazine-1-carboxylate (264 mg).

후처리

  1. washthe organic mixture was washed with saturated sodium hydrogen carbonate, water, and saturated sodium chloride
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-095b4c58d62f4a2d8bbe2ca1897e8abe
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314091B2

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