Toluene → HCID 10883602、化合物

HRID 901168ノート

反応式

HRID 901168 の反応式
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[F: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>[C:23]([C:22]1[CH:21]=[CH:20][C:19]([N:18]([CH2:17][C:16]2[CH:32]=[CH:33][C:34]([O:35][S:1](=[O:4])(=[O:3])[NH2:2])=[C:14]([F:13])[CH:15]=2)[N:27]2[CH:28]=[N:29][N:30]=[CH:31]2)=[CH:26][CH:25]=1)#[N:24]

参加物

7

反応物 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 219769034-[(3-Fluoro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

生成物 1

HCID 10883602HCID 10883602、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

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-Fluoro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB03020, 220 mg, 0.71 mmol) was added to the colourless solution and the mixture was stirred for 4 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 (2×25 mL) and brine (25 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in acetone (5 mL) and precipitated by addition of diethyl ether. The precipitate was filtered off and dried under high vacuum. Yield: 228 mg (83%) white powder. 1H-NMR (400 MHz, d6-DMSO) δ=5.11 (s, 2H), 6.71 (d, J=9.0 Hz, 2H), 7.23 (dd, 8.2, 1.2 Hz, 1H), 7.39 (dd, J=8.2, 8.2 Hz, 1H), 7.43 (dd, J=11.1, 2.1 Hz, 1H), 7.77 (d, J=9.0 Hz, 2H), 8.28 (s, 2H, —NH2), 8.92 (s, 2H). LRMS (FAB+): 389.1 (100, [M+H]+). HRMS (FAB+): 389.08298 C16H14N6O3SF requires 389.083214.

後処理

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water (2×25 mL) and brine (25 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in acetone (5 mL)
  7. customprecipitated by addition of diethyl ether
  8. filtrationThe precipitate was filtered off
  9. customdried under high vacuum

出典と根拠

ORDレコード
ord-a2b6b4270abb4912959274f656100336
出典データセット
uspto-grants-2008_04
特許番号
US07361677B2

反応ノート

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