Thionyl Chloride → HCID 23152326, compound

HRID 1012321Notes

Reaction equation

HRID 1012321 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][C:30]([CH3:35])([CH3:34])[C:31]([OH:33])=O)=[O:28])=[CH:23][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[NH2:40][C:41]1[CH:42]=[C:43]([CH:48]=[CH:49][C:50]=1[NH2:51])[C:44]([O:46][CH3:47])=[O:45].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.N1C=CC=CC=1.O.CO.CN(C)C=O>[NH2:51][C:50]1[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][C:41]=1[NH:40][C:31](=[O:33])[C:30]([NH:29][C:27]([C:24]1[CH:25]=[CH:26][C:8]2[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:16]3[N:10]([CH2:11][CH2:12][O:13][C:14]4[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:15]=43)[C:9]=2[CH:23]=1)=[O:28])([CH3:35])[CH3:34]

Participants

10

Reactant 4

HCID 24386Thionyl ChlorideHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 516892Sodium BicarbonateHCID 23152318HCID 23152318, compound

Product 1

HCID 23152326HCID 23152326, compoundYield 93%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]-2-methylpropionic acid (0.60 g, 1.26 mmol) in chloroform (18.0 ml) was added a catalytic amount of N,N-dimethylformamide, and thionyl chloride (0.28 ml, 3.78 mmol) was added dropwise under ice-cooling. The mixture was stirred for 2 hr. Then, the reaction mixture was evaporated under reduced pressure to give a yellow solid. Further, the obtained solid was dissolved in chloroform (2.5 ml) and added dropwise to a solution of methyl 3,4-diaminobenzoate (0.29 g, 1.76 mmol) in pyridine (1.5 ml) under ice-cooling. After dropwise addition, the mixture was warmed to room temperature, and the mixture was stirred at overnight. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate solution, methanol and water. The precipitate was collected by filtration, washed with water, and dried in vacuo to give methyl 4-amino-3-{2-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]-2-methylpropionylamino}benzoate (0.73 g, yield 93%).

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. customThen, the reaction mixture was evaporated under reduced pressure
  4. customto give a yellow solid
  5. temperaturecooling
  6. additionAfter dropwise addition
  7. stirringthe mixture was stirred at overnight
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-6807b8dc859749feac04943c33f92b1b
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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