HCID 59154175, compound → HCID 57850422, compound

HRID 736673Notes

Reaction equation

HRID 736673 reaction equation
[Br:1][C:2]1[C:3]([S:11][C:12]2[NH:13][C:14]3[C:19]([N:20]=2)=[C:18]([NH2:21])[N:17]=[CH:16][N:15]=3)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.CC1C=CC(S(O[CH2:33][CH2:34][CH:35]2[CH2:40][CH2:39][N:38]([C:41](=[O:62])[C@H:42]([O:44][Si:45]([C:58]([CH3:61])([CH3:60])[CH3:59])([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH3:43])[CH2:37][CH2:36]2)(=O)=O)=CC=1>>[Br:1][C:2]1[C:3]([S:11][C:12]2[N:13]([CH2:33][CH2:34][CH:35]3[CH2:36][CH2:37][N:38]([C:41](=[O:62])[C@H:42]([O:44][Si:45]([C:58]([CH3:59])([CH3:61])[CH3:60])([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)[CH3:43])[CH2:39][CH2:40]3)[C:14]3[C:19]([N:20]=2)=[C:18]([NH2:21])[N:17]=[CH:16][N:15]=3)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

3

Reactant 2

HCID 59154175HCID 59154175, compoundHCID 178508694HCID 178508694, compound

Product 1

HCID 57850422HCID 57850422, compound

Procedure

The alkylation reaction was carried out according to the procedure described for example 1 and 2 using 8-(6-Bromo-benzo[1,3]dioxol-5-ylsulfanyl)-9H-purin-6-ylamine (0.172 g, 0.47 mmol) and 2-[1-((2R)-2-{[tert-butyl-(diphenyl)-silyl]-oxy}-propanoyl)-piperidin-4-yl]-ethyl 4-methylbenzenesulfonate (0.280 g, 0.47 mmol) obtained from step 3 to afford 8-[(6-bromo-1,3-benzodioxol-5-yl)thio]-9-{2-[1-((2R)-2-{[tert butyl(diphenyl)silyl]oxy}propanoyl)piperidin-4-yl]ethyl}-9H-purin-6-amine; LC-MS [M+1]+ 787.1 and 8-[(6-bromo-1,3-benzodioxol-5-yl)thio]-3-{2-[1-((2R)-2-{[tert-butyl(diphenyl)silyl]oxy}propanoyl)piperidin-4-yl]ethyl}-3H-purin-6-amine; LC-MS [M+H]+ 787.1

Workup

  1. customThe alkylation reaction

Sources & evidence

ORD record
ord-3f4470923ea945fbacaeda8a4089258f
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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