Picolyl chloride → HCID 57974351, compound

HRID 1864317Notes

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

Participants

Reactant 2

HCID 23393Picolyl chloride

HCID 69061256HCID 69061256, compound

Product 1

HCID 57974351HCID 57974351, compoundYield 43%

Procedure

The procedure described in Example 3 was repeated using 2-(chloromethyl)pyridine and N-[(1R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)-1-methylethyl]-N-methylacetamide to give the title compound as a light beige solid in 43% yield; NMR spectrum (DMSO-d6 373K) 1.21 (d, 3H), 1.85 (s, 3H), 2.27 (s, 3H), 2.84 (s, 3H), 4.34 (m, 1H), 4.40 (t, 1H), 5.07 (m, 1H), 5.20 (s, 2H), 7.01 (d, 1H), 7.17 (d, 1H), 7.33 (m, 2H), 7.42 (d, 1H), 7.47 (dd, 1H), 7.55 (d, 1H), 7.67 (t, 1H), 7.82 (td, 1H), 8.41 (s, 1H), 8.57 (d, 1H), 9.50 (s, 1H); Mass spectrum MH+ 472.

Sources & evidence

ORD record: ord-2699fb1482614171aa2c2637bf6e111a
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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