1-(3-chloropropyl)pyrrolidine Hydrochloride → 4-(3'-Chloro-4'-fluoroanilino)-6-(3-pyrrolidin-1-ylpropoxy)quinazoline

HRID 1584105Notes

Reaction equation

HRID 1584105 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.[N:22]1([CH2:27][CH2:28][CH2:29]Cl)[CH2:26][CH2:25][CH2:24][CH2:23]1>>[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][CH2:29][CH2:28][CH2:27][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 115719161-(3-chloropropyl)pyrrolidine HydrochlorideHCID 224784324-(3-Chloro-4-fluorophenylamino)quinazolin-6-ol

Product 1

HCID 212239054-(3'-Chloro-4'-fluoroanilino)-6-(3-pyrrolidin-1-ylpropoxy)quinazolineYield 45%

Conditions

Temperature
100 °C

Procedure

Using an analogous procedure to that described in Example 1 except that the reaction mixture was heated to 100° C. for 16 hours, 4-(3'-chloro-4'-fluoroanilino)-6-hydroxyquinazoline was reacted with 3-(pyrrolidin-1-yl)propyl chloride hydrochloride (Chem. Abs., 82, 57736) to give 4-(3'-chloro-4'-fluoroanilino)-6-(3-pyrrolidin-1-ylpropoxy)quinazoline in 45% yield; NMR Spectrum: 1.73 (m, 4H), 2.03 (m, 2H), 2.58 (m, 4H), 2.69 (t, 2H), 4.22 (t, 2H), 7.44 (t, 1H), 7.51 (m, 1H), 7.73 (d, 1H), 7.85 (m, 1H), 7.9 (d, 1H), 8.17 (m, 1H), 8.52 (s, 1H), 9.72 (broad s, 1H); Elemental Analysis: Found C, 62.3; H, 5.9; N. 13.7; C21H22ClFN4O 0.25H2O requires C, 62.2; H, 5.6; N, 13.8%.

Sources & evidence

ORD record
ord-2d30a9e2cd7f4f6e8d3dfda8377380c6
Source dataset
uspto-grants-1999_08
Patent number
US05932574

Reaction notes

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