Picolyl chloride hydrochloride → HCID 57974315, compound

HRID 1864271Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][C@H:21]([CH3:30])[CH2:22][NH:23][C:24](=[O:29])[CH2:25][N:26]([CH3:28])[CH3:27])[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38]Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][C@H:21]([CH3:30])[CH2:22][NH:23][C:24](=[O:29])[CH2:25][N:26]([CH3:27])[CH3:28])[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=1

Participants

Reactant 2

HCID 23392Picolyl chloride hydrochloride

HCID 69059791HCID 69059791, compound

Product 1

HCID 57974315HCID 57974315, compoundYield 59%

Procedure

The procedure described in Example 3 was repeated using N1-[(2R)-2-({4-[(3-chloro-4-hydroxyphenyl)amino]quinazolin-5-yl}oxy)propyl]-N2,N2-dimethylglycinamide and picolyl chloride hydrochloride to give the title compound in 59% yield; NMR spectrum (CDCl3) 1.47 (d, 3H), 2.11 (s, 6H), 2.88 (s, 2H), 3.50-3.63 (m, 1H), 3.64-3.78 (m, 1H), 4.76-4.90 (m, 1H), 5.23 (s, 2H), 6.92-7.00 (m, 2H), 7.13-7.19 (m, 1H), 7.36-7.49 (m, 2H), 7.52-7.72 (m, 4H), 7.90 (d, 1H), 8.55 (m, 2H), 9.82 (s, 1H); Mass spectrum MH+ 521.0.

Sources & evidence

ORD record: ord-c03345c92333411287bcb5a44037ce8f
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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