Trifluoroacetic acid → HCID 85472603, compound

HRID 871104Notes

Reaction equation

HRID 871104 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][N:20]=[C:19]5[NH:23][C:24]([C:26]6[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH:27]=6)=[CH:25][C:18]=45)[CH:15]=[CH:16][C:11]=3[N:10]=[N:9]2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[O:1]1[CH2:2][CH2:3][CH:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][N:20]=[C:19]5[NH:23][C:24]([C:26]6[CH2:31][CH2:30][NH:29][CH2:28][CH:27]=6)=[CH:25][C:18]=45)[CH:15]=[CH:16][C:11]=3[N:10]=[N:9]2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90408458HCID 90408458, compound

Product 1

HCID 85472603HCID 85472603, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 36F (0.315 g, 0.612 mmol) in dichloromethane (8 mL) was treated with trifluoroacetic acid (0.472 mL, 6.12 mmol). The mixture was stirred for 16 hours at room temperature then heated at 40° C. for 4 hours. The reaction was concentrated and the residue was dissolved in 2 mL of methanol and treated slowly with 1.5 mL of 2M HCl in ether. The suspension was stirred for 15 minutes then diluted with ether. The solids were filtered, washed with ether, and vacuum oven dried to give the title compound as the hydrochloride salt. 1H NMR (400 MHz, methanol-d4) δ ppm 1.41-1.60 (m, 4H), 2.33-2.50 (m, 1H), 2.80-2.95 (m, 2H), 3.40 (dd, J=11.4, 3.0 Hz, 1H), 3.51 (t, J=6.1 Hz, 2H), 3.87-4.01 (m, 4H), 4.74 (d, J=7.1 Hz, 2H), 6.55 (dt, J=3.5, 2.0 Hz, 1H), 6.91 (s, 1H), 7.53 (d, J=5.6 Hz, 1H), 7.88 (dd, J=8.7, 1.5 Hz, 1H), 8.11-8.28 (m, 2H), 8.40 (d, J=5.6 Hz, 1H). MS (ESI+) m/z 415.2 (M+H)+.

Workup

  1. temperaturethen heated at 40° C. for 4 hours
  2. concentrationThe reaction was concentrated
  3. dissolutionthe residue was dissolved in 2 mL of methanol
  4. additiontreated slowly with 1.5 mL of 2M HCl in ether
  5. stirringThe suspension was stirred for 15 minutes
  6. additionthen diluted with ether
  7. filtrationThe solids were filtered
  8. washwashed with ether, and vacuum oven
  9. customdried

Sources & evidence

ORD record
ord-a62685cfe58946658e374acb69f5dcae
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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