2-(tert-butylamino)-8-iodo-3-methylquinazolin-4(3H)-one → 2'-(2-(tert-butylamino)-3-methyl-4-oxo-3,4-dihydro-8-quinazolinyl)-1'H-spiro[cyclopropane-1,6'-pyrrolo[3,4-b]pyrrol]-4'(5'H)-one

HRID 1056330Notes

Reaction equation

HRID 1056330 reaction equation
[C:1]([NH:5][C:6]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]2[C:8](=[C:9](I)[CH:10]=[CH:11][CH:12]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:27]2[NH:31][C:30]3[C:32]4([CH2:37][CH2:36]4)[NH:33][C:34](=[O:35])[C:29]=3[CH:28]=2)O1>>[C:1]([NH:5][C:6]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]2[C:8](=[C:9]([C:27]3[NH:31][C:30]4[C:32]5([CH2:37][CH2:36]5)[NH:33][C:34](=[O:35])[C:29]=4[CH:28]=3)[CH:10]=[CH:11][CH:12]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 897821382-(tert-butylamino)-8-iodo-3-methylquinazolin-4(3H)-oneHCID 897834842'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1'H-spiro[cyclopropane-1,6'-pyrrolo[3,4-b]pyrrol]-4'(5'H)-one

Product 1

HCID 897846202'-(2-(tert-butylamino)-3-methyl-4-oxo-3,4-dihydro-8-quinazolinyl)-1'H-spiro[cyclopropane-1,6'-pyrrolo[3,4-b]pyrrol]-4'(5'H)-oneYield 21.1%

Procedure

This compound (35 mg, 21% yield) as a brown solid was prepared according to the procedure described for Example 448, using 2-(tert-butylamino)-8-iodo-3-methylquinazolin-4(3H)-one (701) (157 mg, 0.44 mmol) and 2′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1′H-spiro[cyclopropane-1,6′-pyrrolo[3,4-b]pyrrol]-4′(5′H)-one (707) (157 mg, 0.57 mmol) as the starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.57 (1H, br.), 7.89 (2H, t, J=7.4 Hz), 7.67 (1H, s), 7.19 (1H, t, J=7.6 Hz), 6.81 (1H, s), 5.96 (1H, s), 3.49 (3H, s), 1.50 (9H, s), 1.41 (2H, m), 1.34 (2H, m). m/z (ESI, +ve) 378.0 (M+H)+.

Sources & evidence

ORD record
ord-518506b2bec749bb9947fbafb891d7e4
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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