Hydrochloric Acid → HCID 15521783, compound

HRID 1838225Notes

Reaction equation

HRID 1838225 reaction equation
B.CSC.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH:13]=O)=[CH:8][C:7]=1[C:15]1([CH3:37])[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([Cl:24])[CH:22]=2)[N:17]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=2[O:34][CH3:35])[C:16]1=[O:36].Cl.CO>O1CCCC1>[Cl:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[O:34][CH3:35])[C:16](=[O:36])[C:15]2([C:7]1[CH:8]=[C:9]([NH:12][CH3:13])[CH:10]=[CH:11][C:6]=1[Cl:5])[CH3:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 15521782HCID 15521782, compound

Product 1

HCID 15521783HCID 15521783, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

0.56 ml of a 2M solution of borane-dimethyl sulphide in tetrahydrofuran is added to a solution, cooled to 0° C., of 0.4 g of the compound of Example 67 in 1 ml of tetrahydrofuran. After 1 hour at 58° C. and then cooling to 0° C., 0.2 ml of 10N hydrochloric acid and 1 ml of methanol are added to the reaction mixture. The mixture is heated at 60° C. for 1 hour and cooled, and the solvents are evaporated under reduced pressure. The solid residue is treated with 1 ml of a saturated potassium carbonate solution and extraction is carried out several times with ethyl acetate. The organic phases are dried over anhydrous sodium sulphate and the solvents are evaporated under reduced pressure. Purification is carried out by chromatography on a column of silica gel, elution being carried out with an 85/15 (v/v) cyclohexane/ethyl acetate mixture. The expected product is isolated in the form of the hydrochloride by treating the residue obtained with diethyl ether comprising hydrogen chloride and then filtration is carried out; M.p.=121° C. (0.5H2O.1HCl).

Workup

  1. temperatureThe mixture is heated at 60° C. for 1 hour
  2. temperaturecooled
  3. customthe solvents are evaporated under reduced pressure
  4. additionThe solid residue is treated with 1 ml of a saturated potassium carbonate solution and extraction
  5. dry with materialThe organic phases are dried over anhydrous sodium sulphate
  6. customthe solvents are evaporated under reduced pressure
  7. customPurification
  8. washis carried out by chromatography on a column of silica gel, elution

Sources & evidence

ORD record
ord-f0334874ef7b473286eb9360de167022
Source dataset
uspto-grants-2004_01
Patent number
US06673790B1

Reaction notes

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