1,1,2-Trimethoxyethane → HCID 21217672, compound

HRID 1586009Notes

Reaction equation

HRID 1586009 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([Cl:21])[CH:15]=1.[CH3:22][O:23][CH:24](OC)[CH2:25]OC>>[Cl:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[F:20])[NH:13][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([NH:2][CH2:25][CH2:24][O:23][CH3:22])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 475201,1,2-TrimethoxyethaneHCID 21217673HCID 21217673, compound

Product 1

HCID 21217672HCID 21217672, compoundYield 8%

Procedure

Using an analogous reductive amination procedure to that described in Example 1, 6-amino-4-(3'-chloro-4'-fluoroanilino)quinazoline hydrochloride was reacted with 2-methoxyacetaldehyde dimethyl acetal to give 4-(3'-chloro-4'-fluoroanilino)-6-(2-methoxyethylamino)quinazoline in 8% yield, m.p. 152-154° C.; NMR Spectrum: 3.32 (s, 3H), 3.4 (t, 2H), 3.62 (t, 2H), 6.25 (t, -1H), 7.2 (d, 1H), 7.3 (m, 1H), 7.43 (t, 1H), 7.55 (d, 1H), 7.82 (m, 1H), 8.13 (m, 1H), 8.41 (s, 1H), 9.5 (s, 1H); Elemental Analysis: Found C, 57.9; H, 4.8; N, 15.3; C17H16ClFN4O 0.33H2O 0.1EtOAc requires C, 57.7; H, 4.8; N, 15.5%.

Sources & evidence

ORD record
ord-d849ba548d2047128030ec56ee3e97a7
Source dataset
uspto-grants-1999_08
Patent number
US05942514

Reaction notes

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