Triethylamine → 3-((4-(4-Amino-3-chloro-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

HRID 1878367

반응식

HRID 1878367 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:11])[C:3]=1[Cl:12].[C:13]([NH:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:20]=1)([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(OCC)(=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:29]2[CH2:28][CH2:27][N:26]([CH2:25][C:21]3[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=3)[C:18]([NH:17][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:32])[CH2:31][CH2:30]2)=[O:8])=[C:4]([F:11])[C:3]=1[Cl:12]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 27627744-Amino-3-chloro-2-fluorobenzoic acidHCID 66877987N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide

생성물 1

HCID 579176553-((4-(4-Amino-3-chloro-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide수율 46%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To 4-amino-3-chloro-2-fluorobenzoic acid (0.754 mmol, 143 mg), N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (0.754 mmol, 208 mg) and triethylamine (3.02 mmol, 0.421 ml, 305 mg) in dichloromethane (8 mL) was added 1-propanephosphonic acid cyclic anhydride (1.886 mmol, 1.117 mL, 1200 mg, 50% solution in ethyl acetate). After 2 hours stirring, ethyl acetate was added. The organic solution was washed with saturated sodium hydrogen carbonate, water, and saturated sodium chloride. The organic phase was dried with sodium sulfate, filtered and concentrated. The residue was purified by silica chromatography to yield the title compound (155 mg).

후처리

  1. washThe organic solution was washed with saturated sodium hydrogen carbonate, water, and saturated sodium chloride
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica chromatography

출처 및 근거

ORD 기록
ord-ef4b4b8a7b544ab182341076e62cfe74
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314091B2

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