Trifluoroacetic acid → HCID 16040701, compound

HRID 2193730Notes

Reaction equation

HRID 2193730 reaction equation
[F:1][C:2]1[CH:36]=[C:35]([NH:37][C:38]([N:40]2[CH2:44][CH2:43][N:42]([C:45]3[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=3)[C:41]2=[O:52])=[O:39])[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:32]=[CH:31][C:17]([CH2:18][N:19]([CH2:27][CH2:28][O:29][CH3:30])C(=O)OC(C)(C)C)=[CH:16][CH:15]=3)[S:13][C:6]=12.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:36]=[C:35]([NH:37][C:38]([N:40]2[CH2:44][CH2:43][N:42]([C:45]3[CH:46]=[CH:47][C:48]([F:51])=[CH:49][CH:50]=3)[C:41]2=[O:52])=[O:39])[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH2:18][NH:19][CH2:27][CH2:28][O:29][CH3:30])=[CH:31][CH:32]=3)[S:13][C:6]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58790393HCID 58790393, compound

Product 1

HCID 16040701HCID 16040701, compoundYield 135.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 223 (60 mg, 0.082 mmol) and TFA (1 mL) in toluene (2 mL) was stirred 30 min at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was triturated with diethyl ether, the solid was collected and dried to give the title compound 220 (70 mg, 99.5%) as an off-white solid. 1H NMR (DMSO-d6) δ (ppm): 10.55 (s, 1H), 8.95 (s, broad, 2H), 8.52 (d, J=5.5 Hz, 1H), 8.13 (s, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.84 (dd, J=2.5 and 13.1 Hz, 1H), 7.65-7.61 (m, 4H), 7.49 (t, J=8.8 Hz, 1H), 7.44 (dd, J=2.4 and 8.8 Hz, 1H), 7.30-7.25 (m, 2H), 6.65 (d, J=5.5 Hz, 1H), 4.21 (t, 1H), 3.93 (m, 4H), 3.57 (t, 2H), 3.30 (s, 3H), 3.11 (m, 2H). MS (m/z): 630.3 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was triturated with diethyl ether
  3. customthe solid was collected
  4. customdried

Sources & evidence

ORD record
ord-6b9541b5fce94442b4778cc98a3c1feb
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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