Chloroacetonitrile → HCID 21936064, compound

HRID 1371488Notes

Reaction equation

[Cl:1][C:2]1[C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[C:6]2[O:29][CH2:30][O:31][C:5]2=[CH:4][CH:3]=1.Cl[CH2:33][C:34]#[N:35]>>[Cl:1][C:2]1[C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]4[CH2:24][CH2:25][N:26]([CH2:33][C:34]#[N:35])[CH2:27][CH2:28]4)=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[C:6]2[O:29][CH2:30][O:31][C:5]2=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7856Chloroacetonitrile

HCID 21935986HCID 21935986, compound

Product 1

HCID 21936064HCID 21936064, compound

Procedure

Using an analogous procedure to that described in Example 12, 4-(6-chloro-2,3-methylenedioxyanilino)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazoline was reacted with 2-chloroacetonitrile to give the title compound as a solid; NMR Spectrum: (DMSOd6) 1.65 (m, 2H), 2.1 (m, 2H), 2.2 (m, 1H), 3.15 (m, 2H), 3.6 (m, 2H), 4.05 (s, 3H), 4.15 (m, 2H), 4.55 (s, 2H), 6.15 (s, 2H), 7.05 (d, 1H), 7.15 (d, 1H), 7.4 (s, 1H), 8.15 (s, 1H), 8.9 (s, 1H); Mass Spectrum: M−H− 480 and 482.

Sources & evidence

ORD record: ord-3487ec9d5887476abad3ad084401b58d
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157467B2

Reaction notes

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