Picolyl chloride → HCID 57974359, compound

HRID 1864321Notes

Reaction equation

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

Participants

Reactant 2

HCID 23393Picolyl chloride

HCID 69059090HCID 69059090, compound

Product 1

HCID 57974359HCID 57974359, compoundYield 15%

Procedure

The procedure described in Example 3 was repeated using 2-(chloromethyl)pyridine and 2-hydroxy-N-[(1R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)-1-methylethyl]-N-methylacetamide to give the title compound as a white solid in 15% yield; NMR spectrum (DMSO-d6 373K) 1.25 (d, 3H), 2.28 (s, 3H), 2.83 (s, 3H), 3.96 (s, 2H), 4.35 (m, 1H), 4.46 (t, 1H), 4.97 (m, 1H), 5.19 (s, 2H), 7.01 (d, 1H), 7.18 (d, 2H), 7.33 (m, 2H), 7.44 (m, 1H), 7.56 (d, 1H), 7.68 (t, 1H), 7.83 (td, 1H), 8.40 (s, 1H), 8.58 (d, 1H), 9.48 (s, 1H); Mass spectrum MH+ 488.

Sources & evidence

ORD record: ord-96a57c8de39447af81a906c648b707c7
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

Loading…