3-amino-2-methylquinazolin-4(3H)-one → 2-Methyl-3-[(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-amino]-3H-quinazolin-4-one

HRID 455082Notes

Reaction equation

HRID 455082 reaction equation
Cl.Cl[CH2:3][C:4]1[N:8]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1.[NH2:21][N:22]1[C:31](=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[C:23]1[CH3:33]>>[CH3:33][C:23]1[N:22]([NH:21][CH2:3][C:4]2[N:8]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]3=[N:6][C:5]=2[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:31](=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1

Participants

3

Reactant 2

HCID 2375913-amino-2-methylquinazolin-4(3H)-oneHCID 670287243-(Chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride

Product 1

HCID 670277202-Methyl-3-[(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-amino]-3H-quinazolin-4-one

Procedure

The title compound was prepared according to Method A and the experimentals described for compound 139 from 3-(chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride and 3-amino-2-methylquinazolin-4(3H)-one. m/e+ 410 for C25H24N5O [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 8.31 (s, 1H), 8.22 (t, J=1.1 Hz, 1H), 7.71 (m, 1H), 7.68 (d, J=8.0 Hz, 2H), 7.58 (d, J=8.0 Hz, 1H), 7.53 (d, J=9.1 Hz, 1H), 7.44 (t, J=8.0 Hz, 1H), 7.11 (d, J=8.0 Hz, 2H), 7.06 (dd, J=1.1, 9.1 Hz, 1H), 5.86 (t, J=4.8 Hz, 2H), 4.53 (bs, 1H), 2.42 (s, 3H), 2.33 (s, 3H), 2.29 (s, 3H) ppm; 13C-NMR (100 MHz, CDCl3, δ) 161.838, 155.787, 147.287, 146.870, 144.648, 137.968, 134.753, 131.113, 129.377, 128.399, 128.361, 127.246, 126.736, 126.457, 122.711, 121.779, 120.763, 117.161, 114.044, 43.949, 21.906, 21.459, 18.646 ppm.

Sources & evidence

ORD record
ord-1ed9fd0ed94d494b8a2f9d33ba580da7
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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