1H-Pyrrolo(2,3-b)pyridine → (s)-5-[4-Hydroxyisoxazolidin-2-ylcarbonyl]-3-methyl-1(isobutyl)-6-(1h-pyrrolo[2,3-b]pyridin-1-ylmethyl)thieno[2,3-d]pyrimidine-2,4(1h,3h)-dione

HRID 131568Notes

Reaction equation

HRID 131568 reaction equation
ClC1N=C(C)N([CH2:8][C:9]2[S:24][C:12]3[N:13]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:14](=[O:19])[N:15]([CH3:18])[C:16](=[O:17])[C:11]=3[C:10]=2[C:25]([N:27]2[CH2:31][C@H:30]([OH:32])[CH2:29][O:28]2)=[O:26])C=1Cl.[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][N:41]=2)[CH:36]=[CH:35]1>>[OH:32][C@@H:30]1[CH2:29][O:28][N:27]([C:25]([C:10]2[C:11]3[C:16](=[O:17])[N:15]([CH3:18])[C:14](=[O:19])[N:13]([CH2:20][CH:21]([CH3:22])[CH3:23])[C:12]=3[S:24][C:9]=2[CH2:8][N:34]2[C:42]3=[N:41][CH:40]=[CH:39][CH:38]=[C:37]3[CH:36]=[CH:35]2)=[O:26])[CH2:31]1

Participants

3

Reactant 2

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 101425596-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-5-[4-(S)-hydroxy-2-isoxazolidinylcarbonyl]-3-methyl-1-(isobutyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 10116874(s)-5-[4-Hydroxyisoxazolidin-2-ylcarbonyl]-3-methyl-1(isobutyl)-6-(1h-pyrrolo[2,3-b]pyridin-1-ylmethyl)thieno[2,3-d]pyrimidine-2,4(1h,3h)-dione

Procedure

The subtitle compound was prepared using the procedure described in example 3 part c) from the product of example 3 part b) and 7-azaindole. MS (APCI) 427 [M+H]+. δ 1HCDCl3 0.85 (3H,s), 0.92 (3H,s), 2.15-2.25 (1H,m), 3.38 (3H,s), 3.66 (3H,d), 4.03 (3H,s), 4.97 (s,2H), 5.61 (2H,s), 6.49-6.91 (1H,d), 7.06-7.14 (1H,m), 7.38 (1H,d), 7.91 -7.95 (1H,m) and 8.31-8.37 (1H, m).

Sources & evidence

ORD record
ord-8178a515bb634223b6e6c6f840546816
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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