Methanol → HCID 86641330, compound

HRID 1693295Notes

Reaction equation

HRID 1693295 reaction equation
C([BH3-])#N.[Na+].[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:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:17]([C:18]=43)=[N:16]2)[C:8]=1[CH3:44].CO.[CH:47]1([NH2:50])[CH2:49][CH2:48]1>C(O)(=O)C.O1CCCC1>[CH:47]1([NH:50][CH:21]2[C:22]3[CH2:23][S:24][N:25]=[C:26]([N:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])[C:17]4=[N:16][N:15]([CH2:14][C:9]5[C:8]([CH3:44])=[C:7]([O:6][CH3:5])[C:12]([CH3:13])=[CH:11][N:10]=5)[N:43]=[C:19]([C:18]=34)[CH2:20]2)[CH2:49][CH2:48]1

Participants

7

Reactant 4

HCID 887MethanolHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 67279997HCID 67279997, compound

Product 1

HCID 86641330HCID 86641330, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium cyanoborohydride (1.89 g) 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 (5.71 g), methanol (50 mL), tetrahydrofuran (25 mL), cyclopropylamine (1.04 mL) and acetic acid (1.72 mL) under cooling in an ice bath, and the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure and dissolved in ethyl acetate, and the solution was washed with a saturated sodium bicarbonate solution and then with brine. The organic layer was dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure to obtain the title compound (5.91 g, 97%) as an oil.

Workup

  1. temperatureunder cooling in an ice bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutiondissolved in ethyl acetate
  4. washthe solution was washed with a saturated sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThen, the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-81993eb71adb4fe09fe0485997065909
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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