Trifluoroacetic acid → HCID 90409062, compound

HRID 871089Notes

Reaction equation

HRID 871089 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[NH:21][C:22]([C:24]5[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH:25]=5)=[CH:23][C:16]=34)[CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[NH:21][C:22]([C:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH:25]=5)=[CH:23][C:16]=34)[CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90409408HCID 90409408, compound

Product 1

HCID 90409062HCID 90409062, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 14D (92.0 mg, 0.176 mmol) in dichloromethane (4 mL) was treated with trifluoroacetic acid (0.14 mL, 1.8 mmol) and the mixture was stirred for 3 hours and concentrated. The residue was dissolved in 2 mL of methanol and slowly treated with 3 mL 2M hydrogen chloride in ether. The suspension was stirred for 15 minutes and diluted with ether. The solids were filtered, washed with ether, treated with aqueous sodium bicarbonate, filtered, washed with water and concentrated to give the title compound. 1H NMR (500 MHz, dimethylsulfoxide-d6) δ 2.23-2.29 (m, 2H), 2.92 (t, J=5.6 Hz, 2H), 3.38-3.46 (m, 1H), 5.64 (s, 2H), 6.33 (d, J=1.9 Hz, 1H), 6.53 (s, 1H), 7.11-7.17 (m, 3H), 7.19-7.25 (m, 1H), 7.40 (td, J=7.9, 6.1 Hz, 1H), 7.59 (dd, J=8.3, 1.6 Hz, 1H), 7.83 (d, J=8.3 Hz, 1H), 7.90 (d, J=1.6 Hz, 1H), 8.22 (d, J=5.0 Hz, 1H), 8.54 (s, 1H), 11.81 (bs, 1H) MS (ESI+) m/z 424.2 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 2 mL of methanol
  3. additionslowly treated with 3 mL 2M hydrogen chloride in ether
  4. stirringThe suspension was stirred for 15 minutes
  5. additiondiluted with ether
  6. filtrationThe solids were filtered
  7. washwashed with ether
  8. additiontreated with aqueous sodium bicarbonate
  9. filtrationfiltered
  10. washwashed with water
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-e33b7e22ad0f4cc5842e07fca30ed8dd
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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