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

HRID 829

Reaction equation

HRID 829 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].C[O:16][C:17]1N=C(C)[N:20]=[C:19]([NH:24][C:25](=O)[O:26][C:27]2C=CC=CC=2)[N:18]=1.C1CCN2[C:37](=[N:38][CH2:39]CC2)CC1.Cl>C(#N)C.O>[CH3:27][O:26][C:25]1[N:24]=[C:19]([NH:18][C:17]([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:16])[NH:20][N:38]([CH3:39])[CH:37]=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 19693847Methyl 2-[[[[(4-Methoxy-6-methyl-1,3,6-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-3-carboxylate

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 oil 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-a5a19d2e3ccc4cb7bff13f06f043ffc0
Source dataset
uspto-grants-1998_03
Patent number
US05723410

Linked notes

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