Water → HCID 16722362, compound

HRID 1983183Notes

Reaction equation

HRID 1983183 reaction equation
Cl[C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[O:17][C:16]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:20][C:19]=2[O:30][CH3:31])=[N:15][N:14]=1.[C-:32]#[N:33].[Na+].O>CN(C=O)C>[CH3:31][O:30][C:19]1[CH:20]=[C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:22]=[CH:23][C:18]=1[C:16]1[O:17][C:13]([C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[C:32]#[N:33])=[N:14][N:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 16723117HCID 16723117, compound

Product 1

HCID 16722362HCID 16722362, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-{4-[5-(5-chloro-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-3-methoxy-phenyl }-morpholine (145 mg, 0.33 mmol) in DMF (2 mL) was added sodium cyanide (18 mg, 0.36 mmol) and the mixture was stirred for 18 h at ambient temperature. The resulting yellow-green suspension was treated with water (15 ml) and cooled to 0° C. After stirring for 15 min at 0° C. the suspension was filtered off and washed twice with ice cold water (5 ml) affording the title compound (119 mg, 84%) which was obtained as a yellow solid. MS: m/e=430.3 [M+H]+.

Workup

  1. temperaturecooled to 0° C
  2. stirringAfter stirring for 15 min at 0° C. the suspension
  3. filtrationwas filtered off
  4. washwashed twice with ice cold water (5 ml)

Sources & evidence

ORD record
ord-cc4da3bd2ffd42149bab01b17f846d7a
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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