Phenyl isocyanate → HCID 57600239, compound

HRID 2368630Notes

Reaction equation

HRID 2368630 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]2[C:9](=[O:22])[C:10]3[NH:11][C:12]([Br:21])=[N:13][C:14]=3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:7]2=[N:6][N:5]=1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O.C(#N)C>[Br:21][C:12]1[NH:11][C:10]2[C:9](=[O:22])[N:8]3[C:4]([CH2:3][CH2:2][NH:1][C:30]([NH:29][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:31])=[N:5][N:6]=[C:7]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:14]=2[N:13]=1

Participants

6

Reactant 2

HCID 7672Phenyl isocyanateHCID 57600276HCID 57600276, compound

Product 1

HCID 57600239HCID 57600239, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(2-aminoethyl)-7-bromo-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (62 mg, 0.17 mmol) and phenyl isocyanate (0.018 mL, 0.16 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water and acetonitrile and then purified by preparative LCMS to give the desired product (about 80% conversion). LCMS calculated for C20H24BrN8O2 (M+H): 487.1; 489.1. Found: 487.0, 489.0.

Workup

  1. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-b57d4ed5dfa44f8192410b4596dda2cb
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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