Picolyl chloride → HCID 57974362, compound

HRID 1864306Notes

Reaction equation

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

Participants

Reactant 2

HCID 23393Picolyl chloride

HCID 69060818HCID 69060818, compound

Product 1

HCID 57974362HCID 57974362, compoundYield 43%

Procedure

The procedure described in Example 3 was repeated using 2-(chloromethyl)pyridine and N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]acetamide to give the title compound as a white solid in 43% yield; NMR spectrum (DMSO-d6) 1.41 (d, 3H), 1.77 (s, 3H), 2.27 (s, 3H), 3.41 (dt, 1H), 3.58 (dt, 1H), 4.87 (m, 1H), 5.20 (s, 2H), 7.01 (d, 1H), 7.22 (d, 1H), 7.29 (d, 1H), 7.35 (dd, 1H), 7.55 (m, 2H), 7.58 (dd, 1H), 7.69 (t, 1H), 7.85 (td, 1H), 8.23 (t, 1H), 8.45 (s, 1H), 8.58 (d, 1H), 9.97 (s, 1H); Mass spectrum MH+ 458.

Sources & evidence

ORD record: ord-f12575a2017a47558dbd4762e56af559
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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