Isopropylamine → HCID 86641333, compound

HRID 1693299Notes

Reaction equation

HRID 1693299 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[CH3:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][N:10]=[C:9]([CH2:14][N:15]2[N:43]=[C:19]3[CH2:20][C:21](=O)[C:22]4[CH2:23][S:24][N:25]=[C:26]([N:27](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:17]([C:18]=43)=[N:16]2)[C:8]=1[CH3:44].O1CCCC1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH:1]([NH:4][CH:21]1[C:22]2[CH2:23][S:24][N:25]=[C:26]([NH2:27])[C:17]3=[N:16][N:15]([CH2:14][C:9]4[C:8]([CH3:44])=[C:7]([O:6][CH3:5])[C:12]([CH3:13])=[CH:11][N:10]=4)[N:43]=[C:19]([C:18]=23)[CH2:20]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 67279997HCID 67279997, compound

Product 1

HCID 86641333HCID 86641333, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

Isopropylamine (5.5 μl) was added to a mixture composed of di-tert-butyl {2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-8-oxo-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 40 (30 mg), methanol (0.4 ml), tetrahydrofuran (0.2 ml) and acetic acid (12 μl), and then the mixture was stirred at room temperature for two hours. A solution of sodium cyanoborohydride (10 mg) in methanol (0.4 ml) was added to the reaction mixture, followed by stirring at room temperature overnight. The reaction mixture was concentrated, and a 0.2 N sodium hydroxide solution was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. Dichloromethane (1 ml) and trifluoroacetic acid (0.25 ml) were added to the resulting residue, and the mixture was stirred at room temperature for five hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by NH silica gel chromatography (chloroform-methanol). The resulting oil was dissolved in dioxane, followed by lyophilization to obtain the title compound (6.3 mg, 29%) as an amorphous.

Workup

  1. stirringby stirring at room temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiona 0.2 N sodium hydroxide solution was added to the resulting residue
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionDichloromethane (1 ml) and trifluoroacetic acid (0.25 ml) were added to the resulting residue
  9. stirringthe mixture was stirred at room temperature for five hours
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. customthe resulting residue was purified by NH silica gel chromatography (chloroform-methanol)
  12. dissolutionThe resulting oil was dissolved in dioxane

Sources & evidence

ORD record
ord-acd7aa72526f4266b23888f792bb1bd4
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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