Trifluoroacetic acid → HCID 9979273, compound

HRID 2213364Notes

Reaction equation

HRID 2213364 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([N:22]2[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=O)[O:30]C(C)(C)C)[O:24][C:23]2=[O:36])[CH:12]=[CH:13][C:14]=1[N:15]1[CH:20]=[CH:19][C:18](=[O:21])[CH2:17][CH2:16]1.[Cl:37][CH:38]([Cl:44])C(OCC)=O>ClC(Cl)C>[Cl:37][CH:38]([Cl:44])[C:29]([NH:28][CH2:27][CH:25]1[O:24][C:23](=[O:36])[N:22]([C:11]2[CH:12]=[CH:13][C:14]([N:15]3[CH:20]=[CH:19][C:18](=[O:21])[CH2:17][CH2:16]3)=[C:9]([F:8])[CH:10]=2)[CH2:26]1)=[O:30]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10808Ethyl dichloroacetateHCID 58697742HCID 58697742, compound

Product 1

HCID 9979273HCID 9979273, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

TFA (0.75 mL) is added to a solution of the carbamate from Step 6 of Example 3 (100 mg, 0.247 mmol) in dichloroethane (3.0 mL). This solution is stirred for 1.5 h., and the solvent is removed under vacuum. The residue is dissolved in MeOH (4.0 mL). TEA (105 mg, 1 mmol) is added to the mixture, followed by adding ethyl dichloroacetate (77 mg, 0.49 mmol). The mixture is stirred at r.t. for 16 h. Solvent is removed under vacuum, and the crude product purified by silica gel column chromatography (gradient 1% to 2% MeOH in DCM). MS (m/z): 417 [M+1]+. 1H NMR (300 MHz, DMSO-d6) δ 9.17 (t, J=5.5 Hz, 1H), 7.79 (d, J=14.3 Hz, 1H), 7.69–7.48 (m, 3 H), 6.67 (s, 1H), 5.17 (d, J=7.7 Hz, 1H), 5.05–4.99 (m, 1H), 4.35 (t, J=9.1 Hz, 1H), 4.06 (t, J=7.7 Hz, 3H), 3.93 (dd, J=6.0 and 9.3 Hz, 1H), 3.74–3.72 (m, 2H), 3.51–3.49 (m, 2H).

Workup

  1. customthe solvent is removed under vacuum
  2. dissolutionThe residue is dissolved in MeOH (4.0 mL)
  3. stirringThe mixture is stirred at r.t. for 16 h
  4. customSolvent is removed under vacuum
  5. customthe crude product purified by silica gel column chromatography (gradient 1% to 2% MeOH in DCM)

Sources & evidence

ORD record
ord-fa958f714bee4f7a9b5e93c4706eefe2
Source dataset
uspto-grants-2006_09
Patent number
US07105547B2

Reaction notes

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