Formaldehyde → HCID 58365084, compound

HRID 60260Notes

Reaction equation

HRID 60260 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([CH2:7][O:8][C:9]2[C:17]3[C:16]4[CH:18]=[C:19]([C:22]#[N:23])[N:20]=[CH:21][C:15]=4[N:14]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:13]=3[N:12]=[CH:11][CH:10]=2)[CH2:2]1.C=O.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.C(Cl)Cl.CO>[CH3:34][N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([CH2:7][O:8][C:9]2[C:17]3[C:16]4[CH:18]=[C:19]([C:22]#[N:23])[N:20]=[CH:21][C:15]=4[N:14]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:13]=3[N:12]=[CH:11][CH:10]=2)[CH2:2]1

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58365154HCID 58365154, compound

Product 1

HCID 58365084HCID 58365084, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-4-(piperidin-3-ylmethoxy)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (50 mg, 0.1 mmol) in acetonitrile (0.5 mL) and water (0.1 mL) was added Formalin (0.024 mL, 0.3 mmol) followed by sodium triacetoxyborohydride (48 mg, 0.2 mmol). The reaction mixture was stirred for 20 minutes at ambient temperature and then basified by the addition of saturated aqueous sodium carbonate solution (1 mL), diluted with methylene chloride (50 mL) and methanol (5 mL), and washed with saturated aqueous sodium bicarbonate solution (2×15 mL). The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo to afford a pale yellow solid, which was used in the next step without any further purification (45 mg).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (2×15 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford a pale yellow solid, which
  6. customwas used in the next step without any further purification (45 mg)

Sources & evidence

ORD record
ord-cf373373c03e41c18e968c13ed73be5b
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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