Picolyl chloride hydrochloride → HCID 57974281, compound

HRID 1864264Notes

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]([NH:33][C:34](=[O:37])[CH2:35][OH:36])[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]([NH:33][C:34](=[O:37])[CH2:35][OH:36])[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 69057304HCID 69057304, compound

Product 1

HCID 57974281HCID 57974281, compoundYield 57%

Procedure

The procedure described in Example 3 was repeated using picolyl chloride hydrochloride and N-[(1S)-2-({4-[(3-chloro-4-hydroxyphenyl)amino]quinazolin-5-yl}oxy)-1-methylethyl]-2-hydroxyacetamide to give the title compound in 57% yield; NMR spectrum (DMSO-d6) 1.23 (d, 3H), 3.64-3.81 (m, 2H), 4.24-4.36 (m, 2H), 4.45-4.59 (m, 1H), 5.29 (s, 2H), 5.45 (t, 1H), 7.13-7.23 (m, 2H), 7.35 (t, 2H), 7.49-7.53 (m, 1H), 7.56-7.59 (m, 1H), 7.72 (t, 1H), 7.87 (t, 1H), 7.99-8.02 (m, 2H), 8.46 (s, 1H), 8.59 (d, 1H), 9.75 (s, 1H); Mass spectrum MH+ 493.95.

Sources & evidence

ORD record: ord-f65870f84d7e446398ca63558d180b58
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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