Azepane → 9-[4-(Hexahydro-1H-azepin-yl)butyl]-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine

HRID 590448Notes

Reaction equation

HRID 590448 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C@H:9]([O:13][C:14]1[NH:15][C:16]([NH2:25])=[C:17]2[C:21]([N:22]=1)=[N:20][C:19]([O:23][CH3:24])=[N:18]2)[CH2:10][CH2:11][CH3:12].Br[CH2:27][CH2:28][CH2:29][CH2:30]Cl.[NH:32]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>>[N:32]1([CH2:33][CH2:34][CH2:35][CH2:36][N:20]2[C:19]([O:23][CH3:24])=[N:18][C:17]3[C:21]2=[N:22][C:14]([O:13][C@@H:9]([CH3:8])[CH2:10][CH2:11][CH3:12])=[N:15][C:16]=3[NH2:25])[CH2:38][CH2:37][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 8119AzepaneHCID 813641-Bromo-4-chlorobutaneHCID 178448285HCID 178448285, compound

Product 1

HCID 592526149-[4-(Hexahydro-1H-azepin-yl)butyl]-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine

Procedure

Prepared similarly to Intermediate 36 from 2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-1 H-purin-6-amine trifluoroacetate, 1-bromo-4-chlorobutane, and hexahydro-1H-azepine but with three sequential MDAPs using Method B followed by Method A (×2).

Sources & evidence

ORD record
ord-998bc3cb3093444392b2d79ff342bec5
Source dataset
uspto-grants-2016_01
Patent number
US09233962B2

Reaction notes

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