Trifluoroacetic acid → Benzamide, 4-amino-N-cyclopropyl-

HRID 1943398Notes

Reaction equation

HRID 1943398 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13]C(=O)OC(C)(C)C)=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)=[O:6])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9210177HCID 9210177, compound

Product 1

HCID 38082Benzamide, 4-amino-N-cyclopropyl-Yield 101%

Conditions

Temperature
25 °C

Procedure

To a vial was added tert-butyl 4-(cyclopropylcarbamoyl)phenylcarbamate (326 mg, 1.18 mmol) and TFA (2 mL). The solution was stirred at 25° C. for 1 hour. The solution was concentrated in vacuo to give the crude product mixture which was purified by passing through a SCX column (2 g), eluting with the 2N ammonia in methanol to yield the pure product 4-amino-N-cyclopropylbenzamide (210 mg, 100%). LC/MS, m/z 177.05 (M+1). HPLC Rt, 0.63 min. Waters Sunfire C18 column (4.6×50 mm) 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto give the crude product mixture which
  3. customwas purified
  4. washeluting with the 2N ammonia in methanol

Sources & evidence

ORD record
ord-bb4401b19ace4c4b96dc5cc59ddd0c71
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

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