Triethylamine → Methyl (3-{[[4-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)butyl](2-hydroxy-2-methylpropyl)amino]sulfonyl}phenyl)acetate

HRID 869348Notes

Reaction equation

HRID 869348 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]([O:15]C)=[N:13][C:12]2[C:7]1=[N:8][C:9]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[N:10][C:11]=2[NH2:17].[NH2:23][CH2:24][C:25]([CH3:28])([OH:27])[CH3:26].C(N(CC)CC)C.Cl[S:37]([C:40]1[CH:41]=[C:42]([CH2:46][C:47]([O:49][CH3:50])=[O:48])[CH:43]=[CH:44][CH:45]=1)(=[O:39])=[O:38]>C(#N)C>[NH2:17][C:11]1[N:10]=[C:9]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:8]=[C:7]2[C:12]=1[NH:13][C:14](=[O:15])[N:6]2[CH2:5][CH2:4][CH2:3][CH2:2][N:23]([CH2:24][C:25]([OH:27])([CH3:28])[CH3:26])[S:37]([C:40]1[CH:41]=[C:42]([CH2:46][C:47]([O:49][CH3:50])=[O:48])[CH:43]=[CH:44][CH:45]=1)(=[O:39])=[O:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 231585119-(4-Bromobutyl)-2-butoxy-8-methoxyadenineHCID 23388821Methyl [3-(chlorosulfonyl)phenyl]acetate

Product 1

HCID 11713966Methyl (3-{[[4-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)butyl](2-hydroxy-2-methylpropyl)amino]sulfonyl}phenyl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound obtained in Example 2-13 step (i) (371 mg) and 1-amino-2-methylpropane-2-ol (400 mg) were dissolved in acetonitrile (5 ml) and the same manner to Example 2-19 using triethylamine (0.055 ml) and methyl [3-(chlorosulfonyl)phenyl]acetate (93 mg) was conducted to give the titled compound as a white solid. Yield: 140 mg (24%); mp 192-193° C., MS APCI+ve 579 (M+H).

Sources & evidence

ORD record
ord-e78ef72397974da2b682d925b3d34a98
Source dataset
uspto-grants-2015_03
Patent number
US08969362B2

Reaction notes

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