Benzyl isocyanate → 1-benzyl-3-[6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]urea

HRID 393238Notes

Reaction equation

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

Participants

Reactant 2

HCID 76639Benzyl isocyanate

HCID 222439084-amino-6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazoline

Product 1

HCID 99546491-benzyl-3-[6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]urea

Conditions

Temperature: 35 °C

Procedure

Using an analogous procedure to that described in Example 1 except that the reaction mixture was heated to 35° C. for 16 hours, benzyl isocyanate was reacted with 4-amino-6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazoline to give the title compound; NMR Spectrum: (DMSOd6): 1.3-1.5 (m, 2H), 1.8-1.9 (m, 4H), 1.95 (t, 1H), 2.2 (s, 3H), 2.8 (br d, 2H), 3.9 (br s, 3H), 4.0 (br d, 2H), 4.5 (br d, 2H), 7.2-7.3 (m, 2H), 7.3-7.4 (m, 4H), 8.0 (br s, 1H), 8.55 (br s, 1H), 10.2-10.5 (br s, 1H), 10.4 (t, 1H); Mass Spectrum: M+H+ 436.

Sources & evidence

ORD record: ord-b4f11fcb70f04ef5a8567f235f0d7636
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806274B1

Reaction notes

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