HCID 67040909, compound → HCID 67040343, compound

HRID 605275Notes

Reaction equation

HRID 605275 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)=[O:23])=[CH:17][C:16]=2[NH:29][C:30]2[C:31]3[CH:39]=[CH:38][C:37]([CH:40]([CH3:42])[CH3:41])=[N:36][C:32]=3[N:33]=[CH:34][N:35]=2)=[CH:10][CH:9]=1)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)=[O:23])=[CH:17][C:16]=2[NH:29][C:30]2[C:31]3[CH:39]=[CH:38][C:37]([CH:40]([CH3:41])[CH3:42])=[N:36][C:32]=3[N:33]=[CH:34][N:35]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 67040909HCID 67040909, compound

Product 1

HCID 67040343HCID 67040343, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The product from Example 256d (276 mg, 0.462 mmol) was dissolved in a 1:1 mixture of TFA in CH2Cl2 and stirred at room temperature for 2 hrs. The solvent was removed under vacuum and the crude oil was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (33 mg, 12%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.27-1.35 (m, 6 H), 6.80-6.91 (m, 5 H), 6.99 (d, J=9.19 Hz, 1 H), 7.21-7.25 (m, 1 H), 7.63 (dd, J=8.82, 2.57 Hz, 1 H), 7.81 (d, J=8.46 Hz, 1 H), 7.87 (d, J=4.04 Hz, 1 H), 8.01-8.03 (m, 2 H), 8.82 (s, 1 H), 8.91 (d, J=8.46 Hz, 1 H), 10.39 (s, 1 H) MS (ESI+) m/z 497 (M+TFA+H)+; (ESI−) m/z 495 (M+TFA−H)−.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe crude oil was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (33 mg, 12%)

Sources & evidence

ORD record
ord-613f53efb28742f8b7dbca4cc9926600
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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