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

反応式

HRID 1519465 の反応式
[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

参加物

6

反応物 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 8206Palmitoyl chlorideHCID 216237Tolvaptan

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6e52c18a1d5c46c6a3309d4da8e04d86
出典データセット
uspto-grants-2015_07
特許番号
US09073868B2

関連ノート

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