Toluene → Sulfamic Acid 3-{2-[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-ethylsulfanyl}-phenyl ester

HRID 1685665노트

반응식

HRID 1685665 반응식
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[OH:13][C:14]1[CH:15]=[C:16]([S:20][CH2:21][CH2:22][N:23]([N:32]2[CH:36]=[N:35][N:34]=[CH:33]2)[C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)[CH:17]=[CH:18][CH:19]=1>O.C(OCC)(=O)C.CN(C)C(=O)C>[C:28]([C:27]1[CH:30]=[CH:31][C:24]([N:23]([N:32]2[CH:36]=[N:35][N:34]=[CH:33]2)[CH2:22][CH2:21][S:20][C:16]2[CH:15]=[C:14]([O:13][S:1](=[O:4])(=[O:3])[NH2:2])[CH:19]=[CH:18][CH:17]=2)=[CH:25][CH:26]=1)#[N:29]

참가 물질

7

반응물 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 219769104-{[2-(3-Hydroxy-phenylsulfanyl)-ethyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

생성물 1

HCID 11538931Sulfamic Acid 3-{2-[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-ethylsulfanyl}-phenyl ester

시약·촉매·용매 3

HCID 962Water용매2회HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

Sulphamoyl chloride solution in toluene (1.5 ml, 0.7 M, 1.05 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-dimethyl acetamide (5 ml) was added. 4-{[2-(3-Hydroxy-phenylsulfanyl)-ethyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile (CAB02149, 75 mg, 0.22 mmol) was added to the colourless solution and the mixture was stirred for 18 hours at room temperature. Ethyl acetate (50 ml) and water (50 mL) were added to the solution, the organic layer was separated, washed with water (2×30 ml) and brine (1×20 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 (STX1014) was filtered off and dried under high vacuum. Yield: 79 mg (85%) light yellow powder. 1H-NMR (400 MHz, DMSO-d6) δ3.23 (t, J=7.0 Hz, 2H), 4.07 (t, J=7.0 Hz, 2H), 6.54 (d, J=8.9 Hz, 2H), 7.08-7.12 (m, 1H), 7.20-7.26 (m, 1H), 7.39 (dd, J=9.2, 9.2 Hz, 1H), 7.69 (d, J=8.9 Hz, 2H), 8.03 (s, 2H, —NH2), 8.94 (s, 2H); MS (FAB+): m/z 85.1.1 (28%), 417.0 (100%, [C17H16N6O3S2+H]+); HRMS (FAB+) for C17H17N6O3S2: 417.08036; Found, 417.08067; HPLC tR=1.53 min (99.7%).

후처리

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water (2×30 ml) and brine (1×20 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 (STX1014) was filtered off
  9. customdried under high vacuum

출처 및 근거

ORD 기록
ord-58eeacfd73924f969f7b177c7e93b83f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148415B2

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