1,5-Diazabicyclo(5,4,0)undec-5-ene → HCID 178465982, compound

HRID 1654447Notes

Reaction equation

HRID 1654447 reaction equation
N12CCCCC1C=NCCC2.[CH:12]1([C:15]2[CH:20]=[C:19]([O:21][CH2:22][CH3:23])[NH:18][N:17]([N:24](C3C=CC=CC=3)[C:25](=[O:27])[O-])[N:16]=2)[CH2:14][CH2:13]1.[F:34][CH:35]([F:47])[O:36][C:37]1[C:38]([S:43]([NH2:46])(=[O:45])=[O:44])=[N:39][CH:40]=[CH:41][CH:42]=1>C(#N)C>[F:47][CH:35]([F:34])[O:36][C:37]1[C:38]([S:43]([NH:46][C:25]([NH:24][N:17]2[N:16]=[C:15]([CH:12]3[CH2:13][CH2:14]3)[CH:20]=[C:19]([O:21][CH2:22][CH3:23])[NH:18]2)=[O:27])(=[O:44])=[O:45])=[N:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 20077890HCID 20077890, compoundHCID 178465983HCID 178465983, compound

Product 1

HCID 178465982HCID 178465982, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.63 ml of 1,5-diazabicyclo(5.4.0)undec-5-ene followed by 3.15 g of N-(4-cyclopropyl-6-ethoxy-triazin-2-yl)-phenylcarbamate are added to a solution of 2.24 g of 3-difluoromethoxypyridin-2-yl-sulfonamide in 40 ml of acetonitrile. The reaction mixture is stirred for 45 minutes at room temperature and then concentrated using a rotary evaporator. The oily residue is triturated with 8 ml of 2N hydrochloric acid and diluted with 10 ml of water. The crystal mass is filtered off, washed with water and diethyl ether and dried, yielding 4.05 g of N-(3-difluoromethoxypyridine-2-sulfonyl)-N'-(4-cyclopropyl-6-ethoxy-triazin-2-yl)-urea having a melting point of 144°-145° C.

Workup

  1. concentrationconcentrated
  2. customa rotary evaporator
  3. customThe oily residue is triturated with 8 ml of 2N hydrochloric acid
  4. additiondiluted with 10 ml of water
  5. filtrationThe crystal mass is filtered off
  6. washwashed with water and diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-3b40538ff85442a1891425d87a0ce49a
Source dataset
uspto-grants-1995_04
Patent number
US05407900

Reaction notes

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