Hydrochloric Acid → HCID 69487499, compound

HRID 1271436Notes

Reaction equation

HRID 1271436 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][CH2:17][C:18]3[N:19]=[C:20]([CH:23]=[CH:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[O:21][CH:22]=3)=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[C:35]([BH3-])#N.[Na+].Cl>C(#N)C>[CH3:35][N:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)=[CH:11][CH:12]=1)[CH2:17][C:18]1[N:19]=[C:20]([CH:23]=[CH:24][C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=2)[O:21][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 69487072HCID 69487072, compound

Product 1

HCID 69487499HCID 69487499, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-amine 2 (0.03 g, 0.06 mmol) in acetonitrile (2 ml) formaldehyde (36%, 0.1 ml) and sodium cyanoborohydride (0.012 g, 0.019 mmol) are added. After stirring at room temperature for 10 min the pH is set to 2 by adding conc. hydrochloric acid and stirring is continued for 2 h. The solvents are evaporated, the crude product suspended in water (10 ml) and the pH adjusted to 9 with aqueous ammonia. The mixture is extracted with ethyl acetate (3×25 ml), the organic phase washed with brine and dried over sodium sulfate. After concentration in vacuo the oily residue is precipitated with heptanes to yield methyl-[4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-amine 3 as a light yellow solid. Yield 31 mg (100%); m.p. 112–114° C.

Workup

  1. stirringstirring
  2. waitis continued for 2 h
  3. customThe solvents are evaporated
  4. extractionThe mixture is extracted with ethyl acetate (3×25 ml)
  5. washthe organic phase washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationAfter concentration in vacuo the oily residue
  8. customis precipitated with heptanes

Sources & evidence

ORD record
ord-03553238cec14d18ba8aeeea9350867f
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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