HCID 67040437, compound → HCID 67040585, compound

HRID 605233Notes

Reaction equation

HRID 605233 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]([C:21](=[O:32])[NH:22][C:23]3[S:24][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[N:26][N:27]=3)=[CH:17][C:16]=2[NH:33][C:34]2[C:35]3[CH:43]=[CH:42][C:41]([CH:44]([CH3:46])[CH3:45])=[N:40][C:36]=3[N:37]=[CH:38][N:39]=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:9]=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:22][C:23]3[S:24][C:25]([C:28]([CH3:30])([CH3:31])[CH3:29])=[N:26][N:27]=3)=[O:32])=[CH:17][C:16]=2[NH:33][C:34]2[C:35]3[CH:43]=[CH:42][C:41]([CH:44]([CH3:45])[CH3:46])=[N:40][C:36]=3[N:37]=[CH:38][N:39]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 67040437HCID 67040437, compound

Product 1

HCID 67040585HCID 67040585, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The product from Example 225d (212 mg, 0.323 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 (9 mg, 5%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.34 (d, J=6.99 Hz, 6 H), 1.42 (s, 9 H), 3.21-3.36 (m, 1 H), 6.79-6.87 (m, 2 H), 6.94 (d, J=8.82 Hz, 3 H), 7.86 (d, J=8.46 Hz, 1 H), 8.15 (dd, J=8.82, 2.21 Hz, 1 H), 8.28 (d, J=2.21 Hz, 1 H), 8.88 (s, 1 H), 8.99 (d, J=8.46 Hz, 1 H); MS (ESI+) m/z 555 (M+TFA+H)+; (ESI−) m/z 553 (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 (9 mg, 5%)

Sources & evidence

ORD record
ord-52b72943be3c4774a89b5d0ced0503cf
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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