Nitrogen → HCID 23117115, compound

HRID 1011485Notes

Reaction equation

HRID 1011485 reaction equation
[C:1]12([C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:16][C:15]=3F)=[N:12][OH:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.N#N.[H-].[Na+].O>CN(C=O)C>[C:1]12([C:11]3[C:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:16][C:15]=4[O:13][N:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 24758Sodium hydrideHCID 86626349HCID 86626349, compound

Product 1

HCID 23117115HCID 23117115, compoundYield 94,550.102%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-adamantyl-(4-benzyloxy-2-fluorophenyl)methanone oxime (2.3 mg, 6 mM) in DMF (30 ml) was added at 0° C. dropwise under N2, to a stirred suspension of NaH (0.61 g, 18 mM, 60% oil dispersion) in DMF (10 ml). After the complete addition, the reaction mixture was allowed to warm to room temperature and poured into H2O. The precipitate was collected by filtration to give the expected product (2.06 g, 95%). mp 132° C.

Workup

  1. additionAfter the complete addition
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-eb451be1aacc458b9994d895d9ee1c8a
Source dataset
uspto-grants-2011_07
Patent number
US07977364B2

Reaction notes

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