1,2,3,4-Tetrahydro-3-methyl-1 (isobutyl)-2,4-dioxo-6-(1h-pyrrolo[2,3,b]pyridin-3-ylmethyl)thieno[2,3,d]pyrimidine-5-carboxylic acid → 5-[[4-hydroxyisoxazolidin-2-yl]carbonyl]-3-methyl-1-(isobutyl)-6-[(1H-pyrrolo[2,3,b]pyridin-3-yl)methyl]thieno[2,3,d]pyrimidine-2,4(1H,3H)-dione

HRID 131558Notes

Reaction equation

HRID 131558 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([C:22]([OH:24])=O)=[C:10]([CH2:12][C:13]3[C:21]4[C:16](=[N:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)[S:11][C:5]=2[N:4]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:3]1=[O:29].[OH:30][C@@H:31]1[CH2:35][O:34][NH:33][CH2:32]1>>[OH:30][CH:31]1[CH2:35][O:34][N:33]([C:22]([C:9]2[C:6]3[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:29])[N:4]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:5]=3[S:11][C:10]=2[CH2:12][C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)=[O:24])[CH2:32]1

Participants

3

Reactant 2

HCID 161028771,2,3,4-Tetrahydro-3-methyl-1 (isobutyl)-2,4-dioxo-6-(1h-pyrrolo[2,3,b]pyridin-3-ylmethyl)thieno[2,3,d]pyrimidine-5-carboxylic acidHCID 40531170(S)-isoxazolidin-4-ol

Product 1

HCID 688045125-[[4-hydroxyisoxazolidin-2-yl]carbonyl]-3-methyl-1-(isobutyl)-6-[(1H-pyrrolo[2,3,b]pyridin-3-yl)methyl]thieno[2,3,d]pyrimidine-2,4(1H,3H)-dione

Procedure

The title compound (55 mg) was prepared from the product of step b, (150 mg) by the method of example 1, step g), and (S)-4-hydroxyisoxazolidine, example 1 part b). MS (APCI) 484 [M+H]+. δ 1HDMSO 0.82-0.85 (6H,m), 2.03-2.13 (1H,m), 3.20-3.21 (3H,m), 3.53-3.68 (3H,m), 3.75-3.90 (2H,m), 4.00-4.18 (3H,m), 4.60-4.80 (1H,m), 5.50-5.55 (1H,m), 6.99-7.02 (1H,m), 7.41-7.44 (1H,m), 7.90-7.97 (1H,m), 8.18-8.20 (1H,m), 11.53 (1H,s,br)

Sources & evidence

ORD record
ord-fe969f2766c143ec8920dfb6525ea84b
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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