Acetic Acid → HCID 59134199, compound

HRID 1994395Notes

Reaction equation

HRID 1994395 reaction equation
Cl.[Cl:2][C:3]1[CH:37]=[CH:36][C:6]([CH2:7][CH:8]2[N:13]3[C:14](=[O:31])[CH:15]([NH2:30])[CH2:16][N:17]([S:18]([C:21]4[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=4[O:28][CH3:29])(=[O:20])=[O:19])[CH:12]3[CH2:11][N:10]([CH:32]([CH3:34])[CH3:33])[C:9]2=[O:35])=[CH:5][CH:4]=1.[C:38](O)(=O)[CH3:39].[CH:42](=O)[CH3:43].C([BH3-])#N.[Na+]>CO.C1COCC1>[Cl:2][C:3]1[CH:37]=[CH:36][C:6]([CH2:7][CH:8]2[N:13]3[C:14](=[O:31])[CH:15]([N:30]([CH2:38][CH3:39])[CH2:42][CH3:43])[CH2:16][N:17]([S:18]([C:21]4[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=4[O:28][CH3:29])(=[O:20])=[O:19])[CH:12]3[CH2:11][N:10]([CH:32]([CH3:34])[CH3:33])[C:9]2=[O:35])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68692685HCID 68692685, compound

Product 1

HCID 59134199HCID 59134199, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 mg of 6-(4-chlorobenzyl)-1-(2-methoxy-5-chlorobenzenesulfonyl)-3-amino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione hydrochloride (Example 1) were dissolved in 3 ml of methanol, and 100 μl of acetic acid were added. 100 μl of acetaldehyde and 1 ml of 1M sodium cyanoborohydride solution in THF were added to this solution. After 2 hours, the reaction mixture was evaporated, suspended in 5% Et3N in ethyl acetate and filtered through a small silica gel column. The eluent was evaporated, and the crude substance was dissolved in a mixture of acetonitrile and water and freeze dried. The pure title compound was removed after purification by HPLC. The system and process described under “general processes” was used for this. MW=610.18 (calculated, monoisotopic); measured value (M+H)+: 611.4.

Workup

  1. customthe reaction mixture was evaporated
  2. filtrationfiltered through a small silica gel column
  3. customThe eluent was evaporated
  4. dissolutionthe crude substance was dissolved in a mixture of acetonitrile and water and freeze
  5. customdried
  6. customThe pure title compound was removed
  7. customafter purification by HPLC

Sources & evidence

ORD record
ord-780014412ba6427fb8d0499ebcf04d31
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

Loading…