Acetic Acid → HCID 23498629, compound

HRID 1836206Notes

Reaction equation

HRID 1836206 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:13]2[C:27]3[CH2:28][CH2:29][N:30]([C:32](=[S:45])[NH:33][C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=4[N+:42]([O-:44])=[O:43])[CH2:31][C:26]=3[S:25][C:14]=2[N:15]([CH:20]([CH2:22][CH2:23][CH3:24])[CH3:21])[C:16](=[O:19])[CH2:17][N:18]=1.C(O)C.C([BH3-])#N.[Na+]>O>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]1[NH:18][CH2:17][C:16](=[O:19])[N:15]([CH:20]([CH2:22][CH2:23][CH3:24])[CH3:21])[C:14]2[S:25][C:26]3[CH2:31][N:30]([C:32](=[S:45])[NH:33][C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=4[N+:42]([O-:44])=[O:43])[CH2:29][CH2:28][C:27]=3[C:13]1=2

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 86759506HCID 86759506, compound

Product 1

HCID 23498629HCID 23498629, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Acetic acid (0.5 ml) is added to 0.16 g of 5-(2-chiorophenyl)-1,2,3,6,7,9-hexahydro-N-(4-methoxy-2-nitrophenyl)-2-oxo-1-(2-pentyl)-8H-pyrido[4′,3′:4,5]thieno[2,3-e]-1,4-diazepine-8-carbothioamide (0.26 mmol). Ethanol (3.5 ml) is added to this yellow suspension then acetic acid (1 ml) and finally sodium cyanoborohydride (0.033g, 0.52 mmol) are added dropwise. The reaction mixture is agitated for one hour then it is heated for one hour at 40° C. until solubilization. Then agitation is carried out for 2 hours at 22° C. The reaction medium is poured into ice-cooled water (30 ml), followed by agitation, filtering then washing abundantly with water. After drying under vacuum without heating, the desired product is obtained in the form of an orange powder (0.145 g, 83%)

Workup

  1. waitThen agitation is carried out for 2 hours at 22° C
  2. additionThe reaction medium is poured into ice-
  3. filtrationfiltering
  4. washthen washing abundantly with water
  5. customAfter drying under vacuum
  6. temperaturewithout heating

Sources & evidence

ORD record
ord-94b06dc5c05443099ce163eed0d229d3
Source dataset
uspto-grants-2004_08
Patent number
US06777408B1

Reaction notes

Loading…