Hydrochloric Acid → HCID 22273530, compound

HRID 1064320Notes

Reaction equation

HRID 1064320 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].Cl.CCO[CH2:17][CH3:18].N#CN.[CH3:22][N:23]1[C:27]([C:28]2[CH:33]=[CH:32][N:31]=[C:30](NC3C=CC(S(=O)(=O)N)=CC=3)[N:29]=2)=[CH:26][N:25]=C1.C[O-].[Na+].C(=O)([O-])O.[Na+]>CO.C(#N)C.CC(N(C)C)=O>[CH3:22][N:23]1[C:27]([C:28]2[CH:33]=[CH:32][N:31]=[C:30]([NH:12][C:9]3[CH:10]=[CH:11][C:6]([S:3](=[O:4])(=[O:5])[NH:2][CH3:1])=[CH:7][CH:8]=3)[N:29]=2)=[CH:26][N:25]=[C:17]1[CH3:18]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 9864CyanamideHCID 743684-amino-N-methylbenzene-1-sulfonamideHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 22273540HCID 22273540, compound

Product 1

HCID 22273530HCID 22273530, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

N-Methyl-4-aminobenzenesulphonamide (Method 110; 250 mg, 1.3 mmol) was dissolved in MeOH (3 ml) and 1M HCl in ether (1.3 ml, 1.3 mmol) added. Cyanamide (68 mg, 1.6 mmol) was added along with DMA (0.5 ml). The mixture was heated to 100° C. for 30 min. To this was added 5-(3-dimethylaminoprop-2-en-1-oyl)-1,2-dimethylimidazole (Method 15; 230 mg, 1.2 mmol) and sodium methoxide (150 mg, 2.6 mmol) and heated to 180° C. for 1 hr. The reaction mixture was poured into sat. sodium hydrogen carbonate solution and the resultant solid collected. The solid was triturated with hot DMF and filtered. The filtrate was evaporated in vacuo and purified by flash chromatography on silica gel eluting with DCM/2% methanolic ammonia (100:0 increasing in polarity to 85:15) to yield a white solid which was digested with acetonitrile to yield the title compound as a solid (84 mg, 20%). NMR: 2.38 (d, 6H), 3.95 (s, 3H), 7.19 (d, 2H), 7.63 (s, 1H), 7.68 (d, 2H), 7.93 (d, 2H), 8.43 (d, 1H), 9.91 (s, 1H); m/z 359.

Workup

  1. temperatureheated to 180° C. for 1 hr
  2. customthe resultant solid collected
  3. customThe solid was triturated with hot DMF
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. custompurified by flash chromatography on silica gel eluting with DCM/2% methanolic ammonia (100:0 increasing in polarity to 85:15)
  7. customto yield a white solid which

Sources & evidence

ORD record
ord-240908f8b1034283aa8ee14a69cc62a5
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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