3-(Dimethylamino)propyl chloride hydrochloride → HCID 21223901, compound

HRID 1584104Notes

Reaction equation

HRID 1584104 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:16])[CH:14]=2)[N:9]=[CH:8][N:7]=1.Cl.[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26]Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:26][CH2:25][CH2:24][N:23]([CH3:28])[CH3:22])[CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 224784324-(3-Chloro-4-fluorophenylamino)quinazolin-6-ol

Product 1

HCID 21223901HCID 21223901, compoundYield 72%

Procedure

Using an analogous procedure to that described in Example 1, 4-(3'-chloro-4'-fluoroanilino)-6-hydroxyquinazoline was reacted with 3-dimethylaminopropyl chloride hydrochloride to give 4-(3'-chloro-4'-fluoroanilino)-6-(3-dimethylaminopropoxy)quinazoline in 72% yield; NMR Spectrum: 1.98 (m, 2H), 2.34 (s, 6H), 2.51 (t, 2H), 4.22 (t, 2H), 7.48 (t, 1H), 7.52 (m, 1H), 7.75 (d, 1H), 7.85 (m, 1H), 7.91 (m, 1H), 8.18 (m, 1H), 8.54 (s, 1H), 9.72 (broad s, 1H); Elemental Analysis: Found C, 60.5; H, 5.3; N, 14.9; C19H20ClFN4O requires C, 60.5l; H, 5.3; N, 14.9%.

Sources & evidence

ORD record
ord-837735d5e5ba41119a5ddf9428f97ccb
Source dataset
uspto-grants-1999_08
Patent number
US05932574

Reaction notes

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