Trifluoroacetic acid → HCID 86687132, compound

HRID 630845Notes

Reaction equation

HRID 630845 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]2[N:18]3[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]3=[N:16][N:15]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:23][C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:14]([C@H:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[N:15][N:16]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86687133HCID 86687133, compound

Product 1

HCID 86687132HCID 86687132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A yellow solution of Intermediate 88b (2.01 g, 6.27 mmol) and TFA (11.0 mL, 148 mmol) in DCM (50 mL) was stirred at reflux for 30 min. The cooled solution was concentrated in vacuo, redissolved in MeOH (3 mL), applied to an SCX-2 cartridge (50 g) and washed with MeOH (150 mL). The product was eluted with 2M NH3 in MeOH (100 mL); concentration in vacuo left the title compound as a pale orange solid (1.26 g, 91%). LCMS (Method 3): Rt 0.35 min, m/z 221 [MH+].

Workup

  1. temperatureat reflux for 30 min
  2. concentrationThe cooled solution was concentrated in vacuo
  3. dissolutionredissolved in MeOH (3 mL)
  4. washwashed with MeOH (150 mL)
  5. washThe product was eluted with 2M NH3 in MeOH (100 mL)
  6. concentrationconcentration in vacuo
  7. waitleft the title compound as a pale orange solid (1.26 g, 91%)

Sources & evidence

ORD record
ord-d66bb455b17e49628760e1a209354a95
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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