Acetic Acid → HCID 178484402, compound

HRID 2370732Notes

Reaction equation

HRID 2370732 reaction equation
[Cl:1][C:2]1[C:11]([O:12][C@@H:13]2[CH2:18][CH2:17][C@H:16]([NH2:19])[CH2:15][CH2:14]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C(N(CC)CC)C.C(O)(=O)C.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]=O)=[CH:34][C:33]=1[S:40]([N:43]=[CH:44][N:45]([CH3:47])[CH3:46])(=[O:42])=[O:41].C([BH3-])#N.[Na+]>CO>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][NH:19][C@H:16]2[CH2:15][CH2:14][C@@H:13]([O:12][C:11]3[C:2]([Cl:1])=[C:3]4[C:8](=[CH:9][CH:10]=3)[CH:7]=[N:6][CH:5]=[CH:4]4)[CH2:18][CH2:17]2)=[CH:34][C:33]=1[S:40]([N:43]=[CH:44][N:45]([CH3:46])[CH3:47])(=[O:42])=[O:41]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 539657862-Chloro-N-dimethylaminomethylene-5-formyl-benzenesulfonamideHCID 178511693HCID 178511693, compound

Product 1

HCID 178484402HCID 178484402, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

34 mg (0.11 mmol) cis-4-(5-Chloro-isoquinolin-6-yloxy)-cyclohexylamine (13) were dissolved in 5 ml MeOH and 22 mg (0.22 mmol) triethylamine were added. After the reaction was stirred 30 min, 65 mg (1.1 mmol) acetic acid, 60 mg (0.22 mmol) 2-chloro-N-dimethylaminomethylene-5-formyl-benzenesulfonamide (73) and freshly dried molecular sieves were added and the mixture was stirred for 30 minutes at room temperature. A solution of 20.5 mg (0.33 mmol) sodium cyanoborohydride in 1 ml methanol was added and the mixture was allowed to stand at room temperature overnight. The solvent was removed i. vac. The residue was dissolved in dichloromethane, washed with 1N NaOH and brine, dried over MgSO4 and evaporated. 53 mg of the title compound were isolated as crude product and used without further purification. Rt=0.87 min (Method #4). Detected mass: 535.2/537.1 (M+H+).

Workup

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. waitto stand at room temperature overnight
  3. customThe solvent was removed i
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with 1N NaOH and brine
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-c58bb03f251040f1b9e440bc01107746
Source dataset
uspto-grants-2014_04
Patent number
US08710228B2

Reaction notes

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