Acetic Anhydride → Trifluoroacetic acid

HRID 510930Notes

Reaction equation

HRID 510930 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18].[NH:22]1[CH2:25][CH:24]([C:26]2[C:27]([O:46][CH3:47])=[C:28]([CH:34]([NH:36][C:37]3[N:45]=[CH:44][N:43]=[C:42]4[C:38]=3[N:39]=[CH:40][NH:41]4)[CH3:35])[CH:29]=[C:30]([Cl:33])[C:31]=2[CH3:32])[CH2:23]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[C:1]([N:22]1[CH2:25][CH:24]([C:26]2[C:27]([O:46][CH3:47])=[C:28]([CH:34]([NH:36][C:37]3[N:45]=[CH:44][N:43]=[C:42]4[C:38]=3[N:39]=[CH:40][NH:41]4)[CH3:35])[CH:29]=[C:30]([Cl:33])[C:31]=2[CH3:32])[CH2:23]1)(=[O:3])[CH3:2].[C:17]([OH:19])([C:16]([F:21])([F:20])[F:15])=[O:18]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 178492189HCID 178492189, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178492191HCID 178492191, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (2.0 μL, 0.021 mmol) was added to a solution of N-[1-(3-azetidin-3-yl-5-chloro-2-methoxy-4-methylphenyl)ethyl]-9H-purin-6-amine bis(trifluoroacetate) (8.5 mg, 0.014 mmol, from Example 165) and DIPEA (0.015 mL, 0.085 mmol) in methylene chloride (0.5 mL) at 0° C. and then the reaction was stirred at room temperature for 30 minutes. The crude mixture was purified on prep-LCMS (XBridge C18 Column, eluting with a gradient of acetonitrile in water with 0.05% trifluoroacetic acid, at flow rate of 30 mL/min) to afford the desired product as TFA salt. LCMS calculated for C20H24ClN6O2 (M+H)+: m/z=415.2. found: 415.1

Workup

  1. customThe crude mixture was purified on prep-LCMS (XBridge C18 Column
  2. washeluting with a gradient of acetonitrile in water with 0.05% trifluoroacetic acid, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-a56365692c0f429ab42b482070a74a14
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

Loading…