Hydrochloric Acid → HCID 22715156, compound

HRID 352115Notes

Reaction equation

HRID 352115 reaction equation
CC(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH:11]([NH:16][C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=1[C:27]#[N:28])[CH2:12][CH:13]([CH3:15])[CH3:14])(C)C.Cl.[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].C(O)C>O1CCOCC1>[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].[NH2:7][CH2:8][CH2:9][CH2:10][CH:11]([NH:16][C:17]1[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[CH:19][C:18]=1[C:27]#[N:28])[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 444972Fumaric AcidHCID 69829330HCID 69829330, compound

Product 1

HCID 22715156HCID 22715156, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-[[2-Cyano-5-(trifluoromethyl)phenyl]amino]-6-methylheptylcarbamic acid 1,1-dimethylethyl ester (250 mg, 0.6 mmol) was stirred in a 4M solution of hydrogen chloride in dioxan (15 ml) for 3 h. The mixture was then concentrated to dryness and the residue treated with saturated aqueous sodium carbonate (50 ml). The products were extracted into diethyl ether (100 ml), and the extract dried over magnesium sulphate. Concentration of the extract gave a gum that was purified on silica gel eluting with 10% methanolic ammonia (7N) in dichloromethane. The product from the column was converted into a fumarate salt by addition of one equivalent of fumaric acid in the minimum amount of ethanol. The title compound was isolated as a colourless solid (80 mg, 31%).

Workup

  1. concentrationThe mixture was then concentrated to dryness
  2. additionthe residue treated with saturated aqueous sodium carbonate (50 ml)
  3. extractionThe products were extracted into diethyl ether (100 ml)
  4. dry with materialthe extract dried over magnesium sulphate
  5. customConcentration of the extract gave a gum that
  6. customwas purified on silica gel eluting with 10% methanolic ammonia (7N) in dichloromethane

Sources & evidence

ORD record
ord-47529a1b666b4249980f7855f8a5d340
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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