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 2259192Notes

Reaction equation

HRID 2259192 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). 1H NMR (Me2SO-d6, 200 MHz.) δ: 12.5 (NH), 11.1 (NH), 7.22 (d,1H), 6.60 (d,1H), 4.01 (s,3H), 3.98 (s,3H), 3.71 (s,3H), 2.49 (s,3H).

Workup

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

Sources & evidence

ORD record
ord-12b98f45d10f4f4ab3fcadc4907be904
Source dataset
uspto-grants-1995_12
Patent number
US05472933

Reaction notes

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