Phenol → HCID 66803014, compound

HRID 341453Notes

Reaction equation

HRID 341453 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([CH:21]3[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]3)[O:18][N:17]=2)[N:3]=1.[C:28]1(O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C>C1COCC1>[CH3:15][N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:6]1[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([C:16]2[N:20]=[C:19]([CH:21]3[CH2:26][CH2:25][CH:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:23][CH2:22]3)[O:18][N:17]=2)[N:5]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 66802806HCID 66802806, compound

Product 1

HCID 66803014HCID 66803014, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)cyclohexan-1-ol (Example 424, 0.1 g, 0.272 mmol) in THF (4 mL) was added phenol (0.03 g, 0.272 mmol), triphenylphosphine (0.09 g, 0.327 mmol) and N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide (0.08 g, 0.327 mmol). The reaction mixture was stirred at room temperature 16 h. The mixture was then concentrated and purified by preparative HPLC, Method D, to afford the title compound (0.010 g, 8%).

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified by preparative HPLC, Method D

Sources & evidence

ORD record
ord-15435b2104d2492e94e3134aaa075542
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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