Hydrochloric Acid → 4-Amino-N-{[1-(4-chlorophenyl)cyclopropyl]methyl}-3-fluorobenzamide

HRID 1808246

반응식

HRID 1808246 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CN(C)C=O.C(N(CC)C(C)C)(C)C.[Cl:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]2([CH2:60][NH2:61])[CH2:59][CH2:58]2)=[CH:53][CH:52]=1.Cl>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:61][CH2:60][C:57]2([C:54]3[CH:53]=[CH:52][C:51]([Cl:50])=[CH:56][CH:55]=3)[CH2:59][CH2:58]2)=[O:8])=[CH:4][C:3]=1[F:11]

참가 물질

7

반응물 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 99714-Amino-3-fluorobenzoic acidHCID 81531DiisopropylethylamineHCID 4120166[1-(4-Chlorophenyl)cyclopropyl]methanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 577320174-Amino-N-{[1-(4-chlorophenyl)cyclopropyl]methyl}-3-fluorobenzamide

실험 절차

To a mixture of 4-amino-3-fluorobenzoic acid (180.0 mg, 1.160 mmol) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (HATU, 0.44 g, 1.2 mmol) in N,N-dimethylformamide (2 mL, 20 mmol) at 0° C. were added N,N-diisopropylethylamine (0.61 mL, 3.5 mmol) and C-[1-(4-chloro-phenyl)-cyclopropyl]-methylamine; hydrochloride (303.7 mg, 1.392 mmol). The reaction mixture was slowly warmed to rt. The reaction mixture was quenched with an equal volume of saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic layers were washed successively with water, aqueous lithium chloride, and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified on the Isco (120 g cartridge, chloroform to 12% methanol in chloroform).

후처리

  1. customThe reaction mixture was quenched with an equal volume of saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic layers were washed successively with water, aqueous lithium chloride, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on the Isco (120 g cartridge, chloroform to 12% methanol in chloroform)

출처 및 근거

ORD 기록
ord-0af4449e5f6b4adfaac378c292602afd
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357711B2

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