Isoamyl Nitrite → HCID 58405464, compound

HRID 2093708Notes

Reaction equation

HRID 2093708 reaction equation
N[C:2]1[S:3][C:4]([C:14]2[N:23]=[CH:22][C:21]3[N:20]([CH3:24])[C:19](=[O:25])[C@@H:18]([CH2:26][CH3:27])[N:17]([CH:28]([CH3:30])[CH3:29])[C:16]=3[N:15]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:6]=1.N(OCCC(C)C)=O>C1COCC1>[CH2:26]([C@H:18]1[N:17]([CH:28]([CH3:30])[CH3:29])[C:16]2[N:15]=[C:14]([C:4]3[S:3][CH:2]=[N:6][C:5]=3[C:7]3[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=3)[N:23]=[CH:22][C:21]=2[N:20]([CH3:24])[C:19]1=[O:25])[CH3:27]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 58405418HCID 58405418, compound

Product 1

HCID 58405464HCID 58405464, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-(2-amino-4-(4-fluorophenyl)thiazol-5-yl)-7-ethyl-8-isopropyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 318, 0.14 g, 0.324 mmol) in 1.5 mL anhydrous THF, isoamyl nitrite (0.1 mL, 0.751 mmol) was added. The reaction mixture was place in an oil bath set at 85° C. for 2 h and then concentrated and purified by preparative HPLC. LCMS: 412.2 m/z (M+H)+; ret. Time: 4.84 min (Analytical Method A).

Workup

  1. concentrationconcentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-5d2d4851b674455aa174d544d5bc32b3
Source dataset
uspto-grants-2013_05
Patent number
US08445503B2

Reaction notes

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