Quinazoline → HCID 57777279, compound

HRID 660686Notes

Reaction equation

HRID 660686 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[S:15](=[O:17])(=[O:16])[N:14](CC[Si](C)(C)C)[C:13](=[O:24])[CH2:12]2)=[C:7]([O:25]CC2C=CC=CC=2)[CH:6]=1.C([O:35][C:36](=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[N:43]=[C:44]=[O:45])C.N1C2C(=CC=CC=2)C=NC=1>>[OH:25][C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][CH2:2][N:1]2[C:36](=[O:35])[C:37]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[NH:43][C:44]2=[O:45])[CH:10]=[CH:9][C:8]=1[N:11]1[CH2:12][C:13](=[O:24])[NH:14][S:15]1(=[O:16])=[O:17]

Participants

4

Reactant 3

HCID 9210QuinazolineHCID 522616Ethyl 2-isocyanatobenzoateHCID 68839340HCID 68839340, compound

Product 1

HCID 57777279HCID 57777279, compound

Procedure

The title compound is prepared from 5-[4-(3-aminopropyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one and 2-isocyanatobenzoic acid ethyl ester analogous to Example 214. Cyclization to the quinazoline occurs during the TMS-ethyl deprotection step. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.85 (dq, J=7.71, 7.54 Hz, 2 H) 2.51-2.56 (m, 2 H) 3.92 (d, J=7.33 Hz, 2 H) 4.00 (s, 2 H) 6.63 (dd, J=8.08, 2.02 Hz, 1 H) 6.70 (d, J=2.02 Hz, 1 H) 7.17 (d, J=7.83 Hz, 2 H) 7.26 (d, J=8.08 Hz, 1 H) 7.61 (dd, J=15.41, 1.26 Hz, 1 H) 7.91 (dd, J=8.34, 1.52 Hz, 1 H) 8.93 (br. s., 1 H) 11.36 (br. s., 1 H)

Sources & evidence

ORD record
ord-0bacf475b79743a79d25001e6e3a0b90
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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