Trifluoroacetic acid → HCID 118061505, compound

HRID 920717Notes

Reaction equation

HRID 920717 reaction equation
[C:1]([C:4]1[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[N:6][N:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][C:8]=12)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>ClCCl>[F:26][C:22]1[CH:21]=[C:20]([C:5]2[C:4]([C:1]([NH2:2])=[O:3])=[C:8]3[CH2:9][NH:10][CH2:11][CH2:12][N:7]3[N:6]=2)[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118071100HCID 118071100, compound

Product 1

HCID 118061505HCID 118061505, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 4I (3.0 g, 8.32 mmol) in dichloromethane (20 mL) at 0° C. was added TFA (10.26 mL, 133 mmol) dropwise and stirred at room temperature for 1 h. TFA was removed from the reaction mixture and the residue was quenched with 10% NaHCO3 solution. The solid was filtered to obtain Intermediate 4J (2 g, 92%) as off-white solid, which was used in the next step without purification. MS(ES): m/z=261 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.52-7.57 (m, 1H), 7.46-7.52 (m, 1H), 7.40-7.46 (m, 1H), 7.14-7.27 (m, 2H), 7.08 (bs, 1H), 4.03 (d, J=5.02 Hz, 4H), 3.13 (d, J=5.02 Hz, 2H), 2.64 (d, J=6.02 Hz, 1H).

Workup

  1. customTFA was removed from the reaction mixture
  2. customthe residue was quenched with 10% NaHCO3 solution
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-bc27e37cf4ea43d2afffabfe6ee8b19b
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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