tert-Butanol → HCID 19367588, compound

Reaction equation

[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].C([CH:9]1[CH2:18][CH2:17][C:16]2[NH:15][C:14](=[O:19])[N:13]3[CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])[N:22]=[C:12]3[C:11]=2[CH2:10]1)(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])C=CC=CC=1.C([N:49]([CH2:52]C)CC)C>>[C:1]([O:5][C:52]([NH:49][CH:9]1[CH2:18][CH2:17][C:16]2[NH:15][C:14](=[O:19])[N:13]3[CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])[N:22]=[C:12]3[C:11]=2[CH2:10]1)=[O:37])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 154342809-Carboxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one

Product 1

HCID 19367588HCID 19367588, compound

Procedure

To 10 mL of anhydrous t-butanol was added 9-Carboxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one (327 mg), diphenylphosphorylazide 275 mg), and triethylamine (100 mg). The resulting mixture was refluxed for 14 hours and the solvent removed in vacuo. The mixture was then triterated with 10 mL hot methanol and the resultant solid was collected, washed with ethyl acetate, and dried to yield 9-(t-Butoxycarbonylamino)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one (Compound 28), m.p.>325° C.