Formaldehyde → HCID 86721381, compound

HRID 869548Notes

Reaction equation

HRID 869548 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:33]=1)[O:7][CH2:8][C:9]1[CH:19]=[C:18]([CH2:20][N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[N:23]=[C:22]3[CH2:30][NH:31][CH3:32])[CH:17]=[CH:16][C:10]=1/[C:11]/2=[C:12](/[CH3:15])\[C:13]#[N:14].C=O.[C:36]([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>C(#N)C>[CH3:32][N:31]([CH2:30][C:22]1[N:21]([CH2:20][C:18]2[CH:17]=[CH:16][C:10]3/[C:11](=[C:12](/[CH3:15])\[C:13]#[N:14])/[C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:33][C:6]=4[O:7][CH2:8][C:9]=3[CH:19]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=1)[CH3:36]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 86721382HCID 86721382, compound

Product 1

HCID 86721381HCID 86721381, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

[step 5] (E)-2-[3-fluoro-8-({2-[(methylamino)methyl]-1H-benzo[d]imidazol-1-yl}methyl)dibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (215 mg, 0.49 mmol) obtained in step 4 was dissolved in acetonitrile (9.8 mL), formaldehyde (0.26 mL, 3.43 mmol) and sodium cyanoborohydride (62 mg, 0.98 mmol) were added, and the mixture was stirred at room temperature for 6 hr. To the mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-0/100 v/v) to quantitatively give the title compound (222 mg).

Workup

  1. extractionthe mixture was extracted 3 times with chloroform
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-0/100 v/v)

Sources & evidence

ORD record
ord-4bfaac98d60a4f60b9ed97c75e3d86d5
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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