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

HRID 1184642

Reaction equation

HRID 1184642 reaction equation
[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

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 8206Palmitoyl chlorideHCID 216237Tolvaptan

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9567796359444165a637330ea1574e1c
Source dataset
uspto-grants-2014_03
Patent number
US08669229B2

Linked notes

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