Formaldehyde → HCID 70873478, compound

HRID 2172262Notes

Reaction equation

HRID 2172262 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]([C:42]([F:45])([F:44])[F:43])=[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:48]([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.CO>[CH3:48][N:27]([CH:24]1[CH2:25][CH2:26][N:21]([C:18]2[CH:19]=[CH:20][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:16][CH:17]=2)[CH2:22][CH2:23]1)[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 70873551HCID 70873551, compound

Product 1

HCID 70873478HCID 70873478, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

N-{1-[4-((R)-2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-ylmethoxy)phenyl]piperidin-4-yl}-N-[4-(4-trifluoromethylbenzyloxy)phenyl]amine (0.40 g) and methanol (3 ml) were mixed. A 37% formaldehyde aqueous solution (0.47 g), sodium cyanoborohydride (0.36 g) and acetic acid (3 ml) were added to the mixture and stirred at room temperature overnight. The reaction mixture was added to a potassium carbonate aqueous solution, followed by extraction with methylene chloride. The organic layer was washed with water and dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol=1:0→methylene chloride:methanol=9:1) to afford the title compound as a yellow powder (0.26 g).

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtering
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=1:0→methylene chloride:methanol=9:1)

Sources & evidence

ORD record
ord-343e74104a6547a18f46524eb69f693b
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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