Pyridine → HCID 178475584, compound

HRID 1819432Notes

Reaction equation

HRID 1819432 reaction equation
[N+:1]([C:4]1[C:5]([NH:23][CH2:24][C@H:25]2[CH2:30][CH2:29][C@H:28]([N:31]3[CH2:34][CH:33]([OH:35])[CH2:32]3)[CH2:27][CH2:26]2)=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]([F:22])([F:21])[F:20])=[N:8][CH:9]=1)([O-:3])=[O:2].N1C=CC=CC=1.[C:42](OC(=O)C)(=[O:44])[CH3:43]>>[C:42]([O:35][CH:33]1[CH2:34][N:31]([C@H:28]2[CH2:27][CH2:26][C@H:25]([CH2:24][NH:23][C:5]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]([NH:10][CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[O:18][C:19]([F:21])([F:22])[F:20])[N:6]=3)[CH2:30][CH2:29]2)[CH2:32]1)(=[O:44])[CH3:43]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178526822HCID 178526822, compound

Product 1

HCID 178475584HCID 178475584, compoundYield 18.6%

Conditions

Temperature
20 °C

Procedure

1-(trans-4-{[(5-Nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}cyclohexyl)azetidin-3-ol (25 mg, 0.05 mmol) was dissolved in pyridine (12 μL, 0.15 mmol) and acetic anhydride (14 μL, 0.15 mmol) was added to the solution. The reaction was allowed to stir at 20° C. for 18 h. The volatiles were removed in vacuo and the crude product was purified by flash chromatography on a 12 g SiO2 column, eluting with 90:9:1 CH2Cl2:MeOH:NH4OH as an eluent to afford 5 mg of the title compound, m/z 539.6 [M+1]+

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe crude product was purified by flash chromatography on a 12 g SiO2 column
  3. washeluting with 90:9:1 CH2Cl2

Sources & evidence

ORD record
ord-4ee28f7f4035461b8c65d58ff6134698
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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