Picolyl chloride hydrochloride → HCID 57974334, compound

HRID 1864255Notes

Reaction equation

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

Participants

Reactant 2

HCID 23392Picolyl chloride hydrochloride

HCID 69059114HCID 69059114, compound

Product 1

HCID 57974334HCID 57974334, compoundYield 7%

Procedure

The procedure described in Example 3 was repeated using picolyl chloride hydrochloride and N-[(1R)-2-({4-[(3-chloro-4-hydroxyphenyl)amino]quinazolin-5-yl}oxy)-1-methylethyl]-N-methylacetamide to give the title compound in 7% yield; NMR spectrum (DMSO-d6) 1.18 (d, 3H), 1.83 (s, 3H), 2.84 (s, 3H), 4.19-4.43 (m, 2H), 5.14-5.24 (m, 1H), 5.30 (s, 2H), 7.16-7.27 (m, 2H), 7.32-7.38 (m, 2H), 7.45-7.50 (m, 1H), 7.58 (d, 1H), 7.72 (t, 1H), 7.87 (t, 2H), 8.43 (s, 1H), 8.59 (d, 1H), 9.53 (s, 1H); Mass spectrum MH+ 492.3.

Sources & evidence

ORD record: ord-ca3ef3b9350f46b195b1994d19648620
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

Loading…