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

HRID 562734Notes

Reaction equation

HRID 562734 reaction equation
C(N[C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:26][CH3:27])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:8]([NH2:28])[N:7]=1)CCC.FC(F)(F)C(O)=O.[CH3:36][C@H:37]([O:41]C1NC(N)=C2C(N=1)=NC(OC)=N2)[CH2:38][CH2:39][CH3:40].BrCCCCCl.N1CCCCCC1>>[N:19]1([CH2:18][CH2:17][CH2:16][CH2:15][N:12]2[C:11]([O:26][CH3:27])=[N:10][C:9]3[C:13]2=[N:14][C:6]([O:41][C@@H:37]([CH3:36])[CH2:38][CH2:39][CH3:40])=[N:7][C:8]=3[NH2:28])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 4

HCID 8119AzepaneHCID 813641-Bromo-4-chlorobutaneHCID 59252652N2-Butyl-9-[4-(hexahydro-1H-azepin-1-yl)butyl]-8-(methyloxy)-9H-purine-2,6-diamineHCID 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)-1H-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-1d40e68ecbcd4e5c9d5d72be8d03f8f4
Source dataset
uspto-grants-2011_11
Patent number
US08067426B2

Reaction notes

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