Methyl Isocyanate → 2'-[[(Methylamino)carbonyl]amino]methyl-3-bromo-1,1'-biphenyl-4-methanol

HRID 1740248노트

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HRID 1740248 반응식
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[C:11]([Br:17])[CH:10]=1.[CH3:18][N:19]=[C:20]=[O:21]>C(Cl)Cl.CN(C)C=O.C(OCC)(=O)C>[CH3:18][NH:19][C:20]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[C:11]([Br:17])[CH:10]=1)=[O:21]

참가 물질

6

반응물 2

HCID 12228Methyl IsocyanateHCID 218366552'-Aminomethyl-3-bromo-1,1'-biphenyl-4-methanol

생성물 1

HCID 218368052'-[[(Methylamino)carbonyl]amino]methyl-3-bromo-1,1'-biphenyl-4-methanol수율 88.4%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a solution of 68 mg (0.23 mmol) of 2'-aminomethyl-3-bromo-1,1'-biphenyl-4-methanol (Step H) in 3 mL of dry methylene chloride and 1 mL of dry dimethylformamide under nitrogen atmosphere at 0° C. was added 0.015 mL (0.25 mmol) of methyl isocyanate. The reaction mixture was stirred for 30 minutes at 0° C. then diluted with 100 mL of ethyl acetate, washed with water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried over magnesium sulfate and filtered. The solvent was removed under vacuum to give 71 mg (88%) of the product as a white solid which was used in the next step without further purification. 1H NMR (200 MHz, CD3OD): δ 2.64 (s, 3H), 4.20 (s, 2H), 4.69 (s, 2H), 7.16 (m, 1H), 7.22-7.43 (m, 4H), 7.50 (d, 2 Hz, 1H), 7.58 (d, 8 Hz, 1H). FAB-MS: calculated for C16H17BrN2O2 349; found 349, 351 (80%).

후처리

  1. washwashed with water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-494dc1dc25334ded82140f01e4fc3b5a
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968924

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