2-Hydroxy-gamma-butyrolactone, (2R)- → HCID 57974344, compound

HRID 1864285Notes

Reaction equation

HRID 1864285 reaction equation
[NH2:1][C@H:2]([CH3:30])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[N:25]=[CH:26][S:27][CH:28]=3)=[C:18]([Cl:29])[CH:17]=1)=[N:8][CH:9]=[N:10]2.[OH:31][C@@H:32]1[CH2:37][CH2:36][O:35][C:33]1=[O:34]>>[Cl:29][C:18]1[CH:17]=[C:16]([NH:15][C:7]2[C:6]3[C:11](=[CH:12][CH:13]=[CH:14][C:5]=3[O:4][CH2:3][C@H:2]([NH:1][C:33](=[O:34])[C@H:32]([OH:31])[CH2:37][CH2:36][OH:35])[CH3:30])[N:10]=[CH:9][N:8]=2)[CH:21]=[CH:20][C:19]=1[O:22][CH2:23][C:24]1[N:25]=[CH:26][S:27][CH:28]=1

Participants

3

Reactant 2

HCID 71570702-Hydroxy-gamma-butyrolactone, (2R)-HCID 69058325HCID 69058325, compound

Product 1

HCID 57974344HCID 57974344, compoundYield 73%

Procedure

The procedure described in Example 63 was repeated using 5-{[(2R)-2-aminopropyl]oxy}-N-[3-chloro-4-(1,3-thiazol-4-ylmethoxy)phenyl]quinazolin-4-amine and (R)-(+)-α-hydroxy-γ-butyrolactone to give the title compound in 73% yield; NMR spectrum (DMSO-d6) 1.22 (d, 3H), 1.46-1.61 (m, 1H), 1.72-1.87 (m, 1H), 3.40-3.54 (m, 2H), 3.84-3.97 (m, 1H), 4.19-4.41 (m, 3H), 4.42-4.58 (m, 1H), 5.35 (s, 2H), 5.40 (d, 1H), 7.14 (d, 1H), 7.25-7.38 (m, 2H), 7.53 (dd, 1H), 7.72 (t, 1H), 7.80 (d, 1H), 7.92-8.05 (m, 2H), 8.47 (s, 1H), 9.14 (d, 1H), 9.75 (s, 1H); Mass spectrum MH+ 543.9.

Sources & evidence

ORD record
ord-8fd77fd8515e4bf48450228b13f230bd
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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