Hydrochloric Acid → HCID 14857997, compound

HRID 653992Notes

Reaction equation

HRID 653992 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][N:12]2[C:16](=[O:17])[C:15]([CH3:18])=[C:14]([CH3:19])[C:13]2=[O:20])=[CH:7][C:6]=1[S:21]([NH2:24])(=[O:23])=[O:22])[CH3:2].[CH3:26][O:27][C:28]1[CH:33]=[C:32]([O:34][CH3:35])[N:31]=[C:30]([NH:36][C:37](=O)[O:38]C2C=CC=CC=2)[N:29]=1.N12CCCN=C1CCCCC2.Cl>CN(C)C(=O)C>[CH3:18][C:15]1[C:16](=[O:17])[N:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:25])=[C:6]([S:21]([NH:24][C:37]([NH:36][C:30]3[N:29]=[C:28]([O:27][CH3:26])[CH:33]=[C:32]([O:34][CH3:35])[N:31]=3)=[O:38])(=[O:23])=[O:22])[CH:7]=2)[C:13](=[O:20])[C:14]=1[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 14857993HCID 14857993, compound

Product 1

HCID 14857997HCID 14857997, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

At room temperature, 158 mg (0.43 mmol) of ethyl -2-(aminosulfonyl)-4-[(2,5-dihydro-3,4-dimethyl-2,5-dioxo-1H-pyrrol-1-yl)amino]benzoate and 118 mg (0.43 mmol) of phenyl (4,6-dimethoxypyrimidin-2-yl)carbamate were dissolved in 1.5 ml of N,N-dimethylacetamide. Then, 73 mg of 1,8-diazabicyclo[5.4.0]undec-7-ene were added, followed by stirring for 5 minutes. The resultant mixture was allowed to stand for 15 hours. Thereafter, 0.2 ml of 35% hydrochloric acid was added to 20 ml of ice water, followed by the addition of the reaction mixture in 0.2 ml portions under stirring. After the reaction mixture was stirred for 20 minutes, the resulting precipitate was collected by filtration and dried in air. Using dichloromethane as an eluent, the crude product was purified by chromatography on a column of silica gel ("WAKO GEL C-300", trade name; product of Wako Pure Chemical Industries, Ltd.). Yield: 162 mg (58%). Melting point: 121°-123 ° C. (decomposed). Its physicochemical properties are shown in Table 4.

Workup

  1. waitto stand for 15 hours
  2. additionfollowed by the addition of the reaction mixture in 0.2 ml portions
  3. stirringunder stirring
  4. stirringAfter the reaction mixture was stirred for 20 minutes
  5. filtrationthe resulting precipitate was collected by filtration
  6. customdried in air
  7. customUsing dichloromethane as an eluent, the crude product was purified by chromatography on a column of silica gel ("WAKO GEL C-300", trade name; product of Wako Pure Chemical Industries, Ltd.)

Sources & evidence

ORD record
ord-aacfbf21c30f48d19d09d9d65fee8c6a
Source dataset
uspto-grants-1992_07
Patent number
US05129942

Reaction notes

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