Toluene → (2-chloro-4-{[(4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino]methyl}phenyl) sulfamate

HRID 19921

반응식

HRID 19921 반응식
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:32]=[CH:33][C:34]=1[OH:35])[CH2:17][N:18]([N:27]1[CH:31]=[N:30][N:29]=[CH:28]1)[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1>O.C(OCC)(=O)C.CN(C)C(=O)C>[Cl:13][C:14]1[CH:15]=[C:16]([CH2:17][N:18]([C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[N:27]2[CH:28]=[N:29][N:30]=[CH:31]2)[CH:32]=[CH:33][C:34]=1[O:35][S:1](=[O:4])(=[O:3])[NH2:2]

참가 물질

7

반응물 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 219768724-[(3-Chloro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

생성물 1

HCID 11732219(2-chloro-4-{[(4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino]methyl}phenyl) sulfamate

시약·촉매·용매 3

HCID 962Water용매2회HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

Sulphamoyl chloride solution in toluene (3 mL, 0.7 M, 2.1 mmol) was concentrated under reduced pressure (30° C. water bath temperature) to ca 0.5 mL volume. The residue was cooled to 0° C. (ice bath) and N,N-dimethylacetamide (5 mL) was added. 4-[(3-Chloro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02130, 163 mg, 0.50 mmol) was added to the colourless solution and the mixture was stirred for 18 h at room temperature. Ethyl acetate (50 mL) and water (30 mL) were added to the solution, the organic layer was separated, washed with water (2×30 mL) and brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in a small amount of acetone and precipitated by addition of hexane. The precipitate was filtered off and dried under high vacuum. Yield: 59 mg (29%) white powder. 1H-NMR (400 MHz, d6-DMSO) δ=5.11 (5, 2H), 6.72 (d, J=9.0 Hz, 2H), 7.38 (dd, J=8.2, 2.0 Hz, 1H), 7.44 (d, J=8.2 Hz, 1H), 7.59 (d, J=2.0 Hz, 1H), 7.77 (d, J=9.0 Hz, 2H), 8.31 (s, 2H, —NH2), 8.91 (s, 2H). LRMS (FAB+): 405.0 (100, [M+H]+). HRMS (FAB+) 405.05349 C16H14N6O3SCl requires 405.053663

후처리

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water (2×30 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in a small amount of acetone
  7. customprecipitated by addition of hexane
  8. filtrationThe precipitate was filtered off
  9. customdried under high vacuum

출처 및 근거

ORD 기록
ord-6bf7f7e2239f482ab199abbc70019919
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745472B2

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