Trifluoroacetic acid → HCID 118061505, compound

HRID 920711Notes

Reaction equation

HRID 920711 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, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 1J (3.0 g, 8.32 mmol) in dichloromethane (20 mL) was added TFA (10.26 mL, 133 mmol) dropwise at 0° C. and stirred at room temperature for 3 h. Volatiles were removed, and the residue was quenched with 10% NaHCO3 solution. The off-white solid product 1K (2 g, 92%) was filtered and dried under vacuum and was used in the next step without further purification. MS(ES): m/z=261 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.66-7.73 (m, 2H), 7.22-7.25 (m, 2H), 7.21 (bs, 1H), 7.20 (bs, 1H), 3.98-4.05 (m, 4H), 3.13 (bs, 2H), 2.63 (s, 1H).

Workup

  1. customVolatiles were removed
  2. customthe residue was quenched with 10% NaHCO3 solution
  3. filtrationThe off-white solid product 1K (2 g, 92%) was filtered
  4. customdried under vacuum
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-2bcfe001a3b64d878915ea8c41d9c06f
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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