(+-)-Tetrahydro-2-furoic acid → N-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-N-methyl-tetrahydrofuran-2-carboxamide

HRID 1864228Notes

Reaction equation

HRID 1864228 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([OH:8])=O.[Cl:9][C:10]1[CH:11]=[C:12]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][C:33]=3[O:35][CH2:36][CH2:37][NH:38][CH3:39])[N:28]=[CH:27][N:26]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>>[Cl:9][C:10]1[CH:11]=[C:12]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][C:33]=3[O:35][CH2:36][CH2:37][N:38]([CH3:39])[C:6]([CH:2]3[CH2:3][CH2:4][CH2:5][O:1]3)=[O:8])[N:28]=[CH:27][N:26]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

3

Reactant 2

HCID 86079(+-)-Tetrahydro-2-furoic acidHCID 69065361N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine

Product 1

HCID 11376057N-{2-[(4-{[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-N-methyl-tetrahydrofuran-2-carboxamideYield 89%

Procedure

The procedure described in Example 1 was repeated using tetrahydrofuran-2-carboxylic acid and N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine (obtained as described in Example 1, preparation of starting materials) to give the title compound in 89% yield; NMR spectrum (DMSO-d6) 1.64-1.94 (m, 4H), 3.09 (s, 3H), 3.57-3.70 (m, 2H), 3.82-3.97 (m, 2H), 4.42 (t, 2H), 4.60-4.66 (m, 1H), 5.31 (s, 2H), 7.16 (d, 1H), 7.23 (d, 1H), 7.33 (d, 1H), 7.35-7.39 (m, 1H), 7.52-7.57 (m, 1H), 7.59 (d, 1H), 7.70-7.75 (m, 1H), 7.85-7.91 (m, 1H), 7.92 (d, 1H), 8.42 (s, 1H), 8.61 (d, 1H), 9.70 (s, 1H); Mass spectrum MH+ 534.

Sources & evidence

ORD record
ord-0bd84f06af1a44dca5e5a09d0143342b
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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