Acetone → HCID 59134116, compound

HRID 1994396Notes

Reaction equation

HRID 1994396 reaction equation
[NH2:1][CH:2]1[C:7](=[O:8])[N:6]2[CH:9]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:10](=[O:16])[N:11]([CH:13]([CH3:15])[CH3:14])[CH2:12][CH:5]2[N:4]([S:25]([C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[O:35][CH3:36])(=[O:27])=[O:26])[CH2:3]1.[CH3:37][C:38]([CH3:40])=O.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.C1COCC1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH:9]2[N:6]3[C:7](=[O:8])[CH:2]([NH:1][CH:38]([CH3:40])[CH3:37])[CH2:3][N:4]([S:25]([C:28]4[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=4[O:35][CH3:36])(=[O:27])=[O:26])[CH:5]3[CH2:12][N:11]([CH:13]([CH3:14])[CH3:15])[C:10]2=[O:16])=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 10392919HCID 10392919, compound

Product 1

HCID 59134116HCID 59134116, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 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 (Example 1) were dissolved in ml of methanol, and 200 μl of acetic acid were added. 400 μl of acetone and 1 ml of 1M sodium cyanoborohydride solution in THF were added to this solution. After 3 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=596.16 (calculated, monoisotopic); measured value (M+H)+: 597.3.

Workup

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

Sources & evidence

ORD record
ord-eba976b784a1461f802542e9ed591501
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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