(1S)-2-{4-[2-(6-amino-8-bromo-9H-purin-9-yl)ethyl]piperidin-1-yl}-1-methyl-2-oxoethyl acetate → (1S)-2-[4-(2-{6-Amino-8-[(7-chloro-1,3-benzothiazol-2-yl)thio]-9H-purin-9-yl}ethyl)piperidin-1-yl]-1-methyl-2-oxoethyl acetate

HRID 736676Notes

Reaction equation

HRID 736676 reaction equation
[C:1]([O:4][C@@H:5]([CH3:27])[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[C:24](Br)=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[NH2:26])[CH2:10][CH2:9]1)=[O:7])(=[O:3])[CH3:2].[Cl:28][C:29]1[C:37]2[S:36][C:35]([SH:38])=[N:34][C:33]=2[CH:32]=[CH:31][CH:30]=1>>[C:1]([O:4][C@@H:5]([CH3:27])[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[C:24]([S:38][C:35]3[S:36][C:37]4[C:29]([Cl:28])=[CH:30][CH:31]=[CH:32][C:33]=4[N:34]=3)=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[NH2:26])[CH2:10][CH2:9]1)=[O:7])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 57850528(1S)-2-{4-[2-(6-amino-8-bromo-9H-purin-9-yl)ethyl]piperidin-1-yl}-1-methyl-2-oxoethyl acetateHCID 1785277847-Chloro-2-mercaptobenzothiazole

Product 1

HCID 57850093(1S)-2-[4-(2-{6-Amino-8-[(7-chloro-1,3-benzothiazol-2-yl)thio]-9H-purin-9-yl}ethyl)piperidin-1-yl]-1-methyl-2-oxoethyl acetate

Procedure

The title product was prepared according to the procedure described for example 81 using (1S)-2-{4-[2-(6-amino-8-bromo-9H-purin-9-yl)ethyl]piperidin-1-yl}-1-methyl-2-oxoethyl acetate and 7-chloro-2-mercaptobenzothiazole. LC-MS [M+H]+ 562.1, along with hydrolyzed product, the mixture was used for the next step without any further purification.

Workup

  1. customLC-MS [M+H]+ 562.1, along with hydrolyzed product, the mixture was used for the next step without any further purification

Sources & evidence

ORD record
ord-1027a51521f143dfbd047dcc0e8e2119
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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