Isoamyl Nitrite → HCID 59644539, compound

HRID 2251997Notes

Reaction equation

N[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:9]=[N:10][N:11]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=3)[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1[C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[Cl:42])=[O:35].C(ON=O)CC(C)C>C1COCC1>[F:33][C:30]([F:31])([F:32])[C:22]1[CH:21]=[C:20]([CH:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=1)[CH2:19][N:11]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:8]([C:4]2[C:3]([C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:42])=[O:35])=[CH:2][CH:7]=[CH:6][N:5]=2)[N:9]=[N:10]1

Participants

Conditions

Temperature: 72 °C

Procedure

Dissolve {4-amino-2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chloro-phenyl)-methanone (40.0 mg, 0.067 mmol) in THF (2 mL), add isoamylnitrite (12.0 mg, 13.8 μL, 0.101 mmol) and heat 72° C. for 0.5 h, then cool to RT. Pour the mixture through a plug of Celite® 1 cm and silica gel 2 cm. Concentrate the clear liquid to 1.5 mL and apply to a 2 mm chromatotron plate with CH2Cl2 and EtOAc and elute with a EtOAc/hexane gradient to provide 24 mg of the title compound. Exact Mass 586.1: MS (IS): m/z=586.9 (M+1); 1H NMR (300 MHz, CDCl3) 8.53 (bs, 1H), 7.87 (d, J=7.4 Hz, 1H), 7.72 (s, 1H), 7.45-7.00 (m, 9H), 5.37 (s, 2H).

Workup

temperaturecool to RT
additionPour the mixture through a plug of Celite® 1 cm and silica gel 2 cm
concentrationConcentrate the clear liquid to 1.5 mL
washapply to a 2 mm chromatotron plate with CH2Cl2 and EtOAc and elute with a EtOAc/hexane gradient

Sources & evidence

ORD record: ord-a223a683dd58487eb71dd255eff627e0
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320994B2

Reaction notes

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