O-(2-dimethylaminoethyl)hydroxylamine → HCID 136477620, compound

HRID 2183893Notes

Reaction equation

HRID 2183893 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([CH:17]=O)=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:19]1[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=1.CN(C)CC[O:31][NH2:32]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([CH:17]=[N:32][OH:31])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:19]1[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 4486697O-(2-dimethylaminoethyl)hydroxylamineHCID 87958036HCID 87958036, compound

Product 1

HCID 136477620HCID 136477620, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2′-fluoro-5′-(7-formylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile (100 mg) and O-(2-dimethylaminoethyl)hydroxylamine (150 mg) in ethanol (5 ml) was heated at 55° C. for 16 h then cooled to ambient temperature. The resulting solid was collected by filtration and washed with ice-cold ethanol to give 2′-fluoro-5′-[7-(hydroxyiminomethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile as a white solid (30 mg): δH (360 MHz, DMSO) 7.44 (1H, d, J 7), 7.62-7.73 (2H, m), 7.80 (1H, s), 7.89 (1H, dd, J 8 and 1), 7.90-7.93 (2H, m), 8.06 (1H, dd, J 8 and 1), 8.08 (1H, s), 8.13 (1H, s), 9.05 (1H, d, J 7), 12.25 (1H, s); m/z (ES+) 358 (M++H).

Workup

  1. temperaturethen cooled to ambient temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with ice-cold ethanol

Sources & evidence

ORD record
ord-022fb4d992344ef196e5526a9fa9e415
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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