Hydrochloric Acid → Methyl 2-[[[[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-3-carboxylate

HRID 1081248Notes

Reaction equation

HRID 1081248 reaction equation
[NH2:1][S:2]([C:5]1[N:6]([CH3:14])[CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3].[CH3:15][O:16][C:17]1[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH:24][C:25](=O)[O:26]C2C=CC=CC=2)[N:18]=1.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C.O>[CH3:15][O:16][C:17]1[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH:24][C:25]([NH:1][S:2]([C:5]2[N:6]([CH3:14])[CH:7]=[CH:8][C:9]=2[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3])=[O:26])[N:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11448329Carbamic acid, (4-methoxy-6-methyl-1,3,5-triazin-2-yl)-, phenyl esterHCID 15790330Methyl 2-(aminosulfonyl)-1-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 15790332Methyl 2-[[[[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-3-carboxylateYield 73.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Methyl 2-(aminosulfonyl)-1-methyl-1H-pyrrole-3-carboxylate (0.10 g, 0.46 mmol) and 0.13 g (0.50 mmol) of phenyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate were combined in 2 mL of acetonitrile and 0.075 mL of DBU was added and the resulting amber solution was stirred at ambient temperature for 30 min. The reaction mixture was diluted with 15 mL of water and acidified with 0.5 mL 1N HCl and the resulting precipitate was collected by filtration and rinsed successively with water and ether, then dried to afford 0.13 g of the title compound as a white solid, m.p. 189°-190° C. (dec).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washrinsed successively with water and ether
  3. customdried

Sources & evidence

ORD record
ord-58a144d62464455db9ecb09282cc86f6
Source dataset
uspto-grants-1996_12
Patent number
US05585328

Reaction notes

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