Pyridine → {7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl}hexadecanoate

HRID 1519465

반응식

HRID 1519465 반응식
[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].ClCCl.[CH3:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=1[C:29]([NH:31][C:32]1[CH:33]=[CH:34][C:35]([C:39]([N:41]2[C:47]3[CH:48]=[CH:49][C:50]([Cl:52])=[CH:51][C:46]=3[CH:45]([OH:53])[CH2:44][CH2:43][CH2:42]2)=[O:40])=[C:36]([CH3:38])[CH:37]=1)=[O:30].N1C=CC=CC=1>O>[Cl:52][C:50]1[CH:49]=[CH:48][C:47]2[N:41]([C:39](=[O:40])[C:35]3[CH:34]=[CH:33][C:32]([NH:31][C:29](=[O:30])[C:28]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:22])=[CH:37][C:36]=3[CH3:38])[CH2:42][CH2:43][CH2:44][CH:45]([O:53][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:46]=2[CH:51]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 8206Palmitoyl chlorideHCID 216237Tolvaptan

생성물 1

HCID 86652151{7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl}hexadecanoate수율 74.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Palmitoyl chloride (1.24 ml, 4.4 mmol) was added to a dichloromethane (20 ml) solution of tolvaptan (2.00 g, 4.4 mmol) and pyridine (0.40 ml, 5.0 mmol), and the mixture was stirred at room temperature over night. Water was added to the reaction mixture and the mixture was extracted with dichloromethane. The combined organic layer was washed with water and an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. After filtration and concentration, the residue was purified by silica gel chromatography (n-hexane:ethyl acetate) to thereby obtain 2.25 g (74%) of {7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl}hexadecanoate as amorphous.

후처리

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe combined organic layer was washed with water
  3. dry with materialan aqueous saturated sodium chloride solution, and dried over magnesium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel chromatography (n-hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-6e52c18a1d5c46c6a3309d4da8e04d86
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073868B2

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