HCID 660173, compound → HCID 49872635, compound

HRID 1853411Notes

Reaction equation

HRID 1853411 reaction equation
[NH2:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21]12([CH2:31][C:32](Cl)=[O:33])[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2>>[C:21]12([CH2:31][C:32]([NH:1][N:2]3[C:11](=[O:12])[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[N:4]=[C:3]3[CH2:13][O:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:33])[CH2:28][CH:27]3[CH2:26][CH:25]([CH2:24][CH:23]([CH2:29]3)[CH2:22]1)[CH2:30]2

Participants

3

Reactant 2

HCID 660173HCID 660173, compoundHCID 27718821-Adamantaneacetyl chloride

Product 1

HCID 49872635HCID 49872635, compound

Procedure

3-Amino-2-phenoxymethyl-4(3H)-quinazolinone and 1-adamantaneacetyl chloride were reacted as described in Example 5 to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.50-1.64 (m, 9H), 1.84 (br s, 3H), 2.03-2.15 (m, 2H), 4.96-5.07 (m, 2H), 6.94-7.03 (m, 3H), 7.27-7.34 (m, 2H), 7.59-7.64 (m, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.87-7.92 (m, 1H), 8.18 (dd, J=8.0, 1.2 Hz, 1H), 10.91 (s, 1H) ppm; MS (DCI/NH3) m/z 444 (M+H)+; Elemental Analysis Calculated for C27H29N3O3.H2O: C, 70.26; H, 6.77; N, 9.10. Found: C, 70.17; H, 6.71; N, 9.23.

Sources & evidence

ORD record
ord-44dc7a6043774847950c5df367a92328
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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