Formaldehyde → HCID 70874637, compound

HRID 2172261Notes

Reaction equation

HRID 2172261 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]([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+]>CO.C(O)(=O)C>[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

7

Reactant 4

HCID 712Formaldehyde2×HCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydride2×HCID 70874368HCID 70874368, compound

Product 1

HCID 70874637HCID 70874637, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 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-trifluoromethoxybenzyloxy)phenyl]amine (0.30 g) was suspended in methanol (3 ml). A 37% formaldehyde aqueous solution (0.11 g), sodium cyanoborohydride (89 mg) and acetic acid (1 ml) were added to the suspension and stirred at room temperature for 1 day. A 37% formaldehyde aqueous solution (0.22 g), sodium cyanoborohydride (178 mg) and acetic acid (2 ml) were further added to the mixture and stirred at room temperature for 1 day. The reaction mixture was gradually added to a potassium carbonate aqueous solution, followed by extraction with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by medium pressure silica gel column chromatography (methylene chloride:methanol=10:0→methylene chloride:methanol=9:1) and recrystallized from methanol to afford the title compound as a pale brown powder (0.20 g).

Workup

  1. stirringstirred at room temperature for 1 day
  2. extractionfollowed by extraction with methylene chloride
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over sodium sulfate
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by medium pressure silica gel column chromatography (methylene chloride:methanol=10:0→methylene chloride:methanol=9:1)
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5569fbc1f8fd43819adcb7b09eb79070
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

Loading…