Trifluoroacetic acid → HCID 90412012, compound

HRID 1521987Notes

Reaction equation

HRID 1521987 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:22][CH2:21][N:20]([CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[CH2:19][CH:18]=4)=[CH:16][C:9]=23)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:22][CH2:21][N:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][CH:18]=4)=[CH:16][C:9]=23)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90412116HCID 90412116, compound

Product 1

HCID 90412012HCID 90412012, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 226A (0.43 g, 0.983 mmol) and trifluoroacetic acid (1.817 mL, 23.59 mmol) in dichloromethane (9.83 mL) was stirred at ambient temperature for 24 hours. The mixture was concentrated, dissolved in 5 mL dichloromethane and 2N hydrogen chloride in ether (20 mL) was added. The suspension was stirred for 20 minutes, treated with ether (50 mL), and filtered. The solid was washed with ether and dried under vacuum to afford the title compound as a hydrochloride salt. 1H NMR (400 MHz, DMSO-d6) δ 2.84-2.92 (m, 2H), 3.50-3.63 (m, 2H), 3.74 (s, 3H), 4.03-4.11 (m, 2H), 4.14 (s, 2H), 6.40 (s, 1H), 6.46-6.56 (m, 1H), 7.13 (d, J=5.2 Hz, 1H), 7.16-7.29 (m, 3H), 8.26 (d, J=5.1 Hz, 1H), 12.07 (bs, 1H). MS (ESI+) m/z 382.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in 5 mL dichloromethane
  3. addition2N hydrogen chloride in ether (20 mL) was added
  4. additiontreated with ether (50 mL)
  5. filtrationfiltered
  6. washThe solid was washed with ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ed7acf8926b843ce8ac76b1e29f465c0
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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