HCID 59424621, compound → HCID 59424523, compound

HRID 1261222Notes

Reaction equation

HRID 1261222 reaction equation
[F:1][C:2]1[CH:38]=[C:37]([NH:39][C:40]([NH:42][C:43](=[O:51])[CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[S:41])[CH:36]=[CH:35][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:19]=[CH:18][C:17]([CH2:20][N:21]([CH2:29][CH:30]4[CH2:34][CH2:33][CH2:32][O:31]4)C(=O)OC(C)(C)C)=[CH:16][CH:15]=3)[S:13][C:6]=12>C1(C)C=CC=CC=1.C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:38]=[C:37]([NH:39][C:40]([NH:42][C:43](=[O:51])[CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[S:41])[CH:36]=[CH:35][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:19]=[CH:18][C:17]([CH2:20][NH:21][CH2:29][CH:30]4[CH2:34][CH2:33][CH2:32][O:31]4)=[CH:16][CH:15]=3)[S:13][C:6]=12

Participants

4

Reactant 1

HCID 59424621HCID 59424621, compound

Product 1

HCID 59424523HCID 59424523, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 80 (200 mg, 0.28 mmol) in toluene (5 mL), TFA (excess) was added. The reaction mixture was allowed to stir overnight, the solvent was removed under reduced pressure and the remained solid was triturated with diethyl ether to afford title compound 81 as the di-TFA salt (130 mg, 57% yield). 1H NMR (DMSO) δ (ppm): 12.47 (s, 1H), 11.83 (s, 1H), 9.06 (s, 2H), 8.53 (dd, J=2.0 and 5.5 Hz, 1H), 8.13 (s, 1H), 8.0 (d, J=12.1 Hz, 1H), 7.97 (d, J=8.7 Hz, 2H), 7.63 (d, J=8.2 Hz, 2H), 7.53 (m, 2H), 7.32 (m, 4H), 7.27 (m, 1H), 6.68 (d, J=5.8 Hz, 1H), 4.23 (m, 1H), 3.82 (s, 2H), 3.78 (m, 1H), 3.71 (m, 1H), 3.11 (m, 1H), 2.95 (m, 1H), 2.0 (m, 1H), 1.98 (m, 2H), 1.56 (m, 1H). MS (m/z) 627.3 (M+H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe remained solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-52843ee09a0542fbb8c73bc20a02bccd
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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