Water → (3R)-N-[4'-({[(3-Methoxyphenyl)amino]carbonyl}amino)biphenyl-4-yl]quinuclidine-3-carboxamide hydrochloride

HRID 588351노트

반응식

HRID 588351 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[ClH:19].Cl.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35]([C@@H:37]3[CH:42]4[CH2:43][CH2:44][N:39]([CH2:40][CH2:41]4)[CH2:38]3)=[O:36])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.O>CN(C=O)C>[ClH:19].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:29]=[CH:30][C:31]([NH:34][C:35]([C@@H:37]4[CH:42]5[CH2:41][CH2:40][N:39]([CH2:44][CH2:43]5)[CH2:38]4)=[O:36])=[CH:32][CH:33]=3)=[CH:24][CH:23]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 878433-Methoxyphenyl isocyanateHCID 67427707(3R)-N-(4'-Aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride

생성물 1

HCID 11318130(3R)-N-[4'-({[(3-Methoxyphenyl)amino]carbonyl}amino)biphenyl-4-yl]quinuclidine-3-carboxamide hydrochloride

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

45.4 mg (0.30 mmol) of 3-methoxyphenyl isocyanate and 84.8 μl (0.61 mmol) of triethylamine are added to a solution of 60 mg (0.15 mmol) of ((3R)—N-(4′-aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride (Example 7A) in 0.5 ml of DMF. After 18 h at room temperature, 5 ml of water are added to the reaction mixture. The resulting precipitate is filtered off with suction, washed with water and dried under high vacuum. A preparative HPLC is carried out for further purification. The product fractions are concentrated, mixed with 3 ml of 1 N hydrochloric acid, again concentrated and dried under high vacuum. 22 mg (27.6% of theory) of the title compound are obtained.

후처리

  1. filtrationThe resulting precipitate is filtered off with suction
  2. washwashed with water
  3. customdried under high vacuum
  4. customA preparative HPLC is carried out for further purification
  5. concentrationThe product fractions are concentrated
  6. additionmixed with 3 ml of 1 N hydrochloric acid
  7. concentrationagain concentrated
  8. customdried under high vacuum

출처 및 근거

ORD 기록
ord-7eb247d8dc3b4950bd8b56ea4f90566e
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227964B2

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