1,1-Dichloroethane → HCID 86641327, compound

HRID 1693292Notes

Reaction equation

HRID 1693292 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10][N:11]2[N:39]=[C:15]3[CH2:16][C:17](=O)[C:18]4[CH2:19][S:20][N:21]=[C:22]([N:23]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:13]([C:14]=43)=[N:12]2)[C:4]=1[CH3:40].ClC(Cl)C.[CH3:45][O:46][C:47]1[CH:54]=[C:53]([O:55][CH3:56])[CH:52]=[CH:51][C:48]=1[CH2:49][NH2:50].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(O)(=O)C>[CH3:45][O:46][C:47]1[CH:54]=[C:53]([O:55][CH3:56])[CH:52]=[CH:51][C:48]=1[CH2:49][NH:50][CH:17]1[C:18]2[CH2:19][S:20][N:21]=[C:22]([N:23]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C:13]3=[N:12][N:11]([CH2:10][C:5]4[C:4]([CH3:40])=[C:3]([O:2][CH3:1])[C:8]([CH3:9])=[CH:7][N:6]=4)[N:39]=[C:15]([C:14]=23)[CH2:16]1

Participants

7

Reactant 4

HCID 63651,1-DichloroethaneHCID 5972502,4-DimethoxybenzylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 67279997HCID 67279997, compound

Product 1

HCID 86641327HCID 86641327, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 176Acetic AcidSolvent

Procedure

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 (170 mg), dichloroethane (2 mL), acetic acid (0.034 mL) and 2,4-dimethoxybenzylamine (0.073 mL) was stirred at room temperature for 10 minutes. Then, sodium triacetoxyborohydride (126 mg) was added and the mixture was stirred for two hours. Sodium triacetoxyborohydride (63 mg) was added to the reaction mixture, followed by further stirring for one hour. Methanol (three drops) was added dropwise to the reaction mixture, and then the mixture was separated with chloroform and a 0.5 N sodium hydroxide solution. The aqueous layer was extracted with chloroform, and then the combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methanol-chloroform) to obtain the title compound (108 mg, 50%) as an oil.

Workup

  1. stirringthe mixture was stirred for two hours
  2. stirringby further stirring for one hour
  3. customthe mixture was separated with chloroform
  4. extractionThe aqueous layer was extracted with chloroform
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (methanol-chloroform)

Sources & evidence

ORD record
ord-f387255a409a447d8bc4025d52771880
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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