2-Hydroxy-gamma-butyrolactone, (2R)- → HCID 57974313, compound

HRID 1864280Notes

Reaction equation

HRID 1864280 reaction equation
[NH2:1][C@H:2]([CH3:31])[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[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[C:18]([Cl:30])[CH:17]=1)=[N:8][CH:9]=[N:10]2.[OH:32][C@@H:33]1[CH2:38][CH2:37][O:36][C:34]1=[O:35]>>[Cl:30][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:34](=[O:35])[C@H:33]([OH:32])[CH2:38][CH2:37][OH:36])[CH3:31])[N:10]=[CH:9][N:8]=2)[CH:21]=[CH:20][C:19]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

3

Reactant 2

HCID 71570702-Hydroxy-gamma-butyrolactone, (2R)-HCID 69058267HCID 69058267, compound

Product 1

HCID 57974313HCID 57974313, compoundYield 77%

Procedure

The procedure described in Example 63 was repeated using 5-{[(2R)-2-aminopropyl]oxy}-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine (obtained as described in Example 2.4, preparation of starting materials) and (R)-(+)-α-hydroxy-γ-butyrolactone to give the title compound in 77% yield; NMR spectrum (DMSO-d6) 1.22 (d, 3H), 1.46-1.60 (m, 1H), 1.72-1.86 (m, 1H), 3.38-3.51 (m, 2H), 3.83-3.93 (m, 1H), 4.20-4.40 (m, 3H), 4.42-4.55 (m, 1H), 5.29 (s, 2H), 5.39 (d, 1H), 7.14 (d, 1H), 7.21 (d, 1H), 7.30-7.40 (m, 2H), 7.47-7.55 (m, 1H), 7.58 (d, 1H), 7.72 (t, 1H), 7.87 (t, 1H), 7.97 (d, 1H), 8.01 (s, 1H), 8.46 (s, 1H), 8.59 (d, 1H), 9.74 (s, 1H); Mass spectrum MH+ 538.0.

Sources & evidence

ORD record
ord-2189dbbfdb2946eab71ffb6184302d54
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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