Phosgene → 1-cyclohexyl-3-{[3-[3,6-dihydro-1(2H)-pyridinecarbonyl]-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]sulfonyl}urea

HRID 2398177Notes

Reaction equation

HRID 2398177 reaction equation
[N:1]1([C:7]([N:9]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][C:18]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:19][C:12]=3[CH2:11][CH2:10]2)=[O:8])[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.[CH:24]1([N:30]=[C:31]=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.N1CC=CCC1.C(Cl)(Cl)=O.N1(C(Cl)=O)CC=CCC1.Cl.C1C2C=CC(S(N)(=O)=O)=CC=2CCNC1>>[CH:24]1([NH:30][C:31]([NH:23][S:20]([C:18]2[CH:17]=[CH:16][C:13]3[CH2:14][CH2:15][N:9]([C:7]([N:1]4[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6]4)=[O:8])[CH2:10][CH2:11][C:12]=3[CH:19]=2)(=[O:22])=[O:21])=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 6

HCID 6371PhosgeneHCID 127501,2,3,6-TetrahydropyridineHCID 18502Cyclohexyl isocyanateHCID 130948301,2,3,6-Tetrahydropyridine-1-carbonyl chlorideHCID 214344292,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonamide hydrochlorideHCID 214344383-[3,6-dihydro-1(2H)-pyridinecarbonyl]-2,3,4,5-tetrahydro-1H-3benzazepine-7-sulfonamide

Product 1

HCID 542103041-cyclohexyl-3-{[3-[3,6-dihydro-1(2H)-pyridinecarbonyl]-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]sulfonyl}urea

Procedure

By the reaction of 3-[3,6-dihydro-1(2H)-pyridinecarbonyl]-2,3,4,5-tetrahydro-1H-3benzazepine-7-sulfonamide with cyclohexylisocyanate in a manner analogous to that described in Example 1, there is obtained 1-cyclohexyl-3-{[3-[3,6-dihydro-1(2H)-pyridinecarbonyl]-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-sulfony(} urea, m.p. 173°-174° C. The starting material can be prepared by first reacting 1,2,3,6-tetrahydropyridine with phosgene and subsequently bringing the resulting 3,6-dihydro-1(2H)-pyridinecarbonyl chloride to reaction with 2,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonamide hydrochloride.

Workup

  1. customthere is obtained 1-cyclohexyl-3-{[3-[3,6-dihydro-1(2H)-pyridinecarbonyl]-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-sulfony(} urea, m.p. 173°-174° C
  2. customThe starting material can be prepared

Sources & evidence

ORD record
ord-3049118b2e0942aa87ebfcdd9c00729b
Source dataset
uspto-grants-1977_05
Patent number
US04024128

Reaction notes

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