Methanol → 2-(Aminomethyl)benzamide

HRID 570991Notes

Reaction equation

HRID 570991 reaction equation
NC1N=C2C(N=CN2)=C(OCC2C=CC(C[NH:18][C:19](=[O:34])[C:20]3[CH:25]=[CH:24][C:23](CNC(=O)C(F)(F)F)=[CH:22][CH:21]=3)=CC=2)N=1.CO.C([O-])([O-])=O.[Na+].[Na+].FC(F)(F)C(O)=O.[C:52](#[N:54])C>O>[NH2:54][CH2:52][C:25]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:19]([NH2:18])=[O:34]

Participants

7

Reactant 5

HCID 887MethanolHCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 178508949HCID 178508949, compound

Product 1

HCID 222542712-(Aminomethyl)benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Weighed into a 50 ml round-bottomed flask were 25 mg (50 μmol) of N-(4-((2-amino-9H-purin-6-yloxy)methyl)benzyl)-4-((2,2,2-trifluoroacetamido)methyl)benzamide. 10 ml of methanol, 2 ml of an aqueous solution saturated with Na2CO3 and 4 ml of water were added. It was left stirring overnight at ambient temperature. The deprotection was monitored by HPLC on a Merck Lichrospher RP °18, 5 μm, 125×4.6 column with a gradient of acetonitrile in water containing 0.2% of trifluoroacetic acid.

Workup

  1. customWeighed into a 50 ml round-bottomed flask were
  2. waitIt was left

Sources & evidence

ORD record
ord-ecaa557f6da74bc6ad724f4d1b2391bf
Source dataset
uspto-grants-2015_05
Patent number
US09024022B2

Reaction notes

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