Formaldehyde → HCID 70874576, compound

HRID 2172264Notes

Reaction equation

HRID 2172264 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C@@H:8]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][CH:24]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]5[CH:41]=[CH:40][C:39]([O:42][C:43]([F:46])([F:45])[F:44])=[CH:38][CH:37]=5)=[CH:30][CH:29]=4)[CH2:23][CH2:22]3)=[CH:17][CH:16]=1)[O:7]2)([O-:3])=[O:2].C=O.[C:49](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[CH3:49][N:27]([CH:24]1[CH2:23][CH2:22][N:21]([C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C@H:8]3[O:7][C:6]4=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][N:11]4[CH2:10][CH2:9]3)=[CH:20][CH:19]=2)[CH2:26][CH2:25]1)[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([O:42][C:43]([F:46])([F:45])[F:44])=[CH:40][CH:41]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 712Formaldehyde2×HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 70873490HCID 70873490, compound

Product 1

HCID 70874576HCID 70874576, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-{1-[4-((S)-2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-ylmethoxy)phenyl]piperidin-4-yl}-N-[4-(4-trifluoromethoxybenzyloxy)phenyl]amine (0.30 g) was suspended in 1,2-dichloroethane (2 ml). A 37% formaldehyde aqueous solution (0.362 ml) and sodium triacetoxyborohydride (149 mg) were added to the suspension and stirred at room temperature overnight. A 37% formaldehyde aqueous solution (0.362 ml) and sodium triacetoxyborohydride (149 mg) were further added thereto and stirred at room temperature for 1 day. A sodium hydrogen carbonate aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1→methylene chloride:methanol=4:1) and crystallized from ether to afford the title compound as a pale yellow powder (130 mg).

Workup

  1. stirringstirred at room temperature for 1 day
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1→methylene chloride:methanol=4:1)
  6. customcrystallized from ether

Sources & evidence

ORD record
ord-ae6312df87864a0396ffc9c709d95a47
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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