(1-Methylcyclopropyl)amine hydrochloride → 8-iodo-3-methyl-2-((1-methylcyclopropyl)amino)quinazolin-4(3H)-one
Reaction equation
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]1([CH3:17])C[CH2:15][CH2:14]1)[N:8]([CH3:18])[C:7]2=[O:19].ClC1N(C)C(=O)C2C(=C(I)C=CC=2)N=1.Cl.CC1(N)CC1>>[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]1([CH3:17])[CH2:15][CH2:14]1)[N:8]([CH3:18])[C:7]2=[O:19]Participants
4
Procedure
This compound (0.71 g, 80% yield) as a yellow crystalline solid was prepared according to the procedure described for intermediate 711, using 2-chloro-8-iodo-3-methylquinazolin-4(3H)-one (700) (0.80 g, mmol), 1-methylcyclopropanamine hydrochloride (ChemBridge, San Diego, Calif.; 0.471 g, 4.38 mmol), and TEA (2.1 mL, 15.10 mmol) as the starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.14 (1H, dd, J=7.5, 1.3 Hz), 7.93 (1H, dd, J=7.9, 1.3 Hz), 7.49 (1H, s), 6.89 (1H, t, J=7.7 Hz), 3.32 (3H, m), 1.58 (3H, s), 0.84 (2H, m), 0.74 (2H, m). m/z (ESI, +ve) 355.9 (M+H)+).
Sources & evidence
- ORD record
- ord-eac1e9d4ab994896842ad82762275c5a
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394297B2
Reaction notes
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