3-Fluorobenzyl chloride → HCID 57974306, compound

HRID 1864304Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1.[OH:10][CH2:11][C:12]([NH:14][CH2:15][C@H:16]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[C:21]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([CH3:37])[CH:31]=1)=[N:22][CH:23]=[N:24]2)[CH3:17])=[O:13]>>[F:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][O:36][C:33]1[CH:34]=[CH:35][C:30]([NH:29][C:21]2[C:20]3[C:25](=[CH:26][CH:27]=[CH:28][C:19]=3[O:18][C@H:16]([CH3:17])[CH2:15][NH:14][C:12](=[O:13])[CH2:11][OH:10])[N:24]=[CH:23][N:22]=2)=[CH:31][C:32]=1[CH3:37]

Participants

Reactant 2

HCID 99743-Fluorobenzyl chloride

HCID 69056760HCID 69056760, compound

Product 1

HCID 57974306HCID 57974306, compoundYield 25%

Procedure

The procedure described in Example 3 was repeated using 1-(chloromethyl)-3-fluorobenzene and 2-hydroxy-N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]acetamide (obtained as described in Example 82, preparation of starting materials) to give the title compound as a light yellow solid in 25% yield; NMR spectrum (DMSO-d6) 1.39 (d, 3H), 2.25 (s, 3H), 3.42 (dt, 1H), 3.72 (dt, 1H), 3.81 (d, 2H), 4.94 (m, 1H), 5.17 (s, 2H), 5.47 (t, 1H), 6.99 (d, 1H), 7.16 (td, 1H), 7.22 (d, 1H), 7.30 (m, 3H), 7.43 (m, 1H), 7.56 (d, 1H), 7.61 (dd, 1H), 7.68 (t, 1H), 8.16 (t, 1H), 8.43 (s, 1H), 9.94 (s, 1H); Mass spectrum MH+ 491.

Sources & evidence

ORD record: ord-43942c28edb34d67af35e2b91681032a
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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