Formaldehyde → HCID 118093811, compound

HRID 1056968Notes

Reaction equation

HRID 1056968 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([CH3:18])[C:7](=[O:17])[N:8]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:4]=2[C:3]=1[O:21][CH2:22][CH:23]1[CH2:26][CH2:25][CH2:24]1.C=O.O.[C:30]([BH3-])#N.[Na+]>O1CCCC1>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([CH3:18])[C:7](=[O:17])[N:8]([CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][N:14]([CH3:30])[CH2:15][CH2:16]3)[C:4]=2[C:3]=1[O:21][CH2:22][CH:23]1[CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 118093891HCID 118093891, compound

Product 1

HCID 118093811HCID 118093811, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-4-(cyclobutylmethoxy)-1-methyl-3-(2-piperazin-1-ylethyl)-1,3-dihydro-2H-benzimidazol-2-one (40.0 mg, 0.0945 mmol) in tetrahydrofuran (2.0 mL) was treated with a 1.23M solution of formaldehyde in water (384 μL, 0.474 mmol). The resultant reaction mixture was stirred at RT for 30 min, followed by the addition of sodium cyanoborohydride (17.8 mg, 0.284 mmol). After stirring at RT for 2 h, the reaction mixture was quenched with acetic acid (0.5 mL) and concentrated in vacuo to give the crude product. Purification via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min) gave the desired product (38 mg, 92%). LCMS calculated for C20H30BrN4O2 (M+H)+: m/z=437.2, 439.2. found: 437.1, 439.1.

Workup

  1. customThe resultant reaction mixture
  2. stirringAfter stirring at RT for 2 h
  3. customthe reaction mixture was quenched with acetic acid (0.5 mL)
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customPurification via preparative LCMS (XBridge C18 column
  7. washeluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-30f7ee5bffbe4deb9d30992aea74559a
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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