tert-Butanol → HCID 19367588, compound

HRID 1939632Notes

Reaction equation

HRID 1939632 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

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 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.

Workup

  1. temperatureThe resulting mixture was refluxed for 14 hours
  2. customthe solvent removed in vacuo
  3. customthe resultant solid was collected
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-e6c998f0be9a4c93ba8efbb7f34f17dc
Source dataset
uspto-grants-1997_12
Patent number
US05696260

Reaction notes

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