6-Bromomethyl-3,4-dihydro-4-oxo-3-((pivaloyl)oxy)methylquinazoline → Diethyl N-(2-fluoro-4-(N-((3,4-dihydro-4-oxo-3((pivaloyl)oxy)methyl-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-L-glutamate

HRID 2254572Notes

Reaction equation

HRID 2254572 reaction equation
[F:1]C1C=C(NCC#C)C=CC=1C(N[C@H](C(OCC)=O)CCC(OCC)=O)=O.[O:28]=[C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([CH2:39][N:40]([CH2:63][C:64]#[CH:65])[C:41]3[CH:62]=[CH:61][C:44]([C:45]([NH:47][C@H:48]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])=[O:46])=[CH:43][CH:42]=3)[CH:37]=2)[N:32]=[CH:31][N:30]1[CH2:66][O:67][C:68](=[O:73])[C:69]([CH3:72])([CH3:71])[CH3:70].BrCC1C=C2C(=CC=1)N=CN(COC(=O)C(C)(C)C)C2=O>>[F:1][C:61]1[CH:62]=[C:41]([N:40]([CH2:63][C:64]#[CH:65])[CH2:39][C:36]2[CH:37]=[C:38]3[C:33](=[CH:34][CH:35]=2)[N:32]=[CH:31][N:30]([CH2:66][O:67][C:68](=[O:73])[C:69]([CH3:71])([CH3:70])[CH3:72])[C:29]3=[O:28])[CH:42]=[CH:43][C:44]=1[C:45]([NH:47][C@H:48]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])=[O:46]

Participants

4

Reactant 3

HCID 136912136-Bromomethyl-3,4-dihydro-4-oxo-3-((pivaloyl)oxy)methylquinazolineHCID 13691215Diethyl N-(4-(N-((3,4-dihydro-4-oxo-3-((pivaloyl)oxy) methyl-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-L-glutamateHCID 14730572Diethyl N-(2-fluoro-4-(N-prop-2-ynylamino)benzoyl)-L-glutamate

Product 1

HCID 14730576Diethyl N-(2-fluoro-4-(N-((3,4-dihydro-4-oxo-3((pivaloyl)oxy)methyl-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-L-glutamate

Procedure

The compound was prepared from compound (9) in a similar manner to that for the preparation of compound (5) from compound (4) in Example 1 using the reagent quantities and conditions set out in Table A.

Sources & evidence

ORD record
ord-873d4085b5224f0793c6920dff159445
Source dataset
uspto-grants-1993_08
Patent number
US05236927

Reaction notes

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