Isatoic Anhydride → HCID 178453285, compound

HRID 1818966Notes

Reaction equation

HRID 1818966 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[NH:20])SC)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[C:22]12[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=1)[NH:27]C(=O)O[C:23]2=[O:24].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[NH:27][C:28]3[C:22]([C:23](=[O:24])[N:20]=2)=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 10340Sodium CarbonateHCID 178503995HCID 178503995, compound

Product 1

HCID 178453285HCID 178453285, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of compound 79.3 (1.5 mmol), isatoic anhydride (1.5 mmol), and Na2CO3 (3.0 mmol) in dioxane (15 mL) was stirred at 100° C. for 8 hours. The solvent was removed and the residue was diluted with 20 mL of water. Subsequently, the suspension was filtered and the white solid was washed sequentially with water and ether, and then dried in vacuo to give {2-[4-(4-oxo-1,4-dihydro-quinazolin-2-ylamino)-phenyl]-ethyl}-carbamic acid tert-butyl ester (compound 79.4) in 52% yield. 1H NMR (d6-DMSO, 400 MHz): δ 10.77 (s, 1H), 8.60 (s, 1H), 7.92 (d, J=7.3 Hz, 1H), 7.59 (m, 3H), 7.35 (d, J=8.3 Hz, 1H), 7.12-7.20 (m, 3H), 6.86 (s, 1H), 3.09 (t, J=7.1 Hz, 2H), 2.62 (t, J=7.1 Hz, 2H), 1.34 (s, 9H) ppm; EIMS (m/z): 381.2 (M++H).

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with 20 mL of water
  3. filtrationSubsequently, the suspension was filtered
  4. washthe white solid was washed sequentially with water and ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6366db07911b43ffa03fc1cc01a1371e
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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