4-(3-Chloropropyl)morpholine → HCID 21223902, compound

HRID 1584106Notes

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.[O:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29]Cl)[CH2:23][CH2:22]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:24]3[CH2:25][CH2:26][O:21][CH2:22][CH2:23]3)[CH:14]=2)[N:9]=[CH:8][N:7]=1

Participants

Reactant 2

HCID 958344-(3-Chloropropyl)morpholine

HCID 224784324-(3-Chloro-4-fluorophenylamino)quinazolin-6-ol

Product 1

HCID 21223902HCID 21223902, compoundYield 58%

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 2 hours. 4-(3'-chloro-4'- fluoroanilino)-6-hydroxyquinazoline was reacted with 3-morpholinopropyl chloride to give 4-(3'-chloro-4'-fluoranilino)-6-(3-morpholinopropoxy)quinazoline in 58% yield; NMR Spectrum: 1.97 (m, 2H), 2.4 (broad t, 4H), 2.48 (t, 2H), 3.58 (t, 4H), 4.2 (t, 2H), 7.44 (t, 1H), 7.53 (m, 1H) 7.74 (d, 1H), 7.85 (m, 1H), 7.9 (d, 1H), 8.17 (m, 1H), 8.53 (s, 1H), 9.67 (broad s, 1H); Elemental Analysis: Found C, 60.0; H, 5.4; N, 13.2; C21H22ClFN4O2 0.2H2O requires C, 60.0; H, 5.3; N, 13.3%.

Sources & evidence

ORD record: ord-7d6489cc92d048eda6c0c5d1300518d9
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932574

Reaction notes

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