Formaldehyde → HCID 25127537, compound

HRID 1672774Notes

Reaction equation

HRID 1672774 reaction equation
[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([N:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)[CH:23]=3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:30]=1)[CH3:2].C=O.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([N:24]4[CH2:29][CH2:28][N:27]([CH3:33])[CH2:26][CH2:25]4)[CH:23]=3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:30]=1)[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67350105HCID 67350105, compound

Product 1

HCID 25127537HCID 25127537, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(S)-9-Ethylamino-5-[5-(piperazine-1-yl)pyridin-3-yl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (56.1 mg, 0.137 mmol) obtained in Step 2 was dissolved in 1,2-dichloroethane (4 mL), and the mixture was stirred at room temperature for 1 hour after adding 37% formalin solution (0.0310 mL, 0.411 mmol) and sodium triacetoxyborohydride (87.0 mg, 0.411 mmol). Thereafter, a saturated aqueous sodium bicarbonate solution was added to the mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (Compound 42) (43.0 mg, 74%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a53b172a6ae048168f99a239c29cf855
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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