3-Fluorobenzyl chloride → HCID 57974314, compound

HRID 1864309Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][C:26]=3[O:28][C@H:29]([CH3:35])[CH2:30][NH:31][C:32](=[O:34])[CH3:33])[N:21]=[CH:20][N:19]=2)=[CH:13][C:12]=1[CH3:36]>>[F:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][C:26]=3[O:28][C@H:29]([CH3:35])[CH2:30][NH:31][C:32](=[O:34])[CH3:33])[N:21]=[CH:20][N:19]=2)=[CH:13][C:12]=1[CH3:36]

Participants

Reactant 2

HCID 99743-Fluorobenzyl chloride

HCID 69060818HCID 69060818, compound

Product 1

HCID 57974314HCID 57974314, compoundYield 46%

Procedure

The procedure described in Example 3 was repeated using 1-(chloromethyl)-3-fluorobenzene and N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]acetamide (obtained as described in Example 86, preparation of starting materials) to give the title compound as a white solid in 46% yield; NMR spectrum (DMSO-d6) 1.41 (d, 3H), 1.77 (s, 3H), 2.26 (s, 3H), 3.41 (dt, 1H), 3.58 (dt, 1H), 4.86 (m, 1H), 5.18 (s, 2H), 7.01 (d, 1H), 7.16 (td, 1H), 7.22 (d, 1H), 7.30 (m, 3H), 7.42 (m, 1H), 7.54 (d, 1H), 7.62 (dd, 1H), 7.68 (t, 1H), 8.22 (t, 1H), 8.43 (s, 1H), 9.95 (s, 1H); Mass spectrum MH+ 475.

Sources & evidence

ORD record: ord-3942d3f1ddba4c229f4266cad201ec84
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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