HCID 67040322, compound → HCID 67040920, compound

HRID 605204Notes

Reaction equation

HRID 605204 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:33])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:17][C:16]=2[NH:34][C:35]2[C:36]3[CH:44]=[CH:43][C:42]([CH:45]([CH3:47])[CH3:46])=[N:41][C:37]=3[N:38]=[CH:39][N:40]=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]([C:21]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][CH:24]=3)=[O:33])=[CH:17][C:16]=2[NH:34][C:35]2[C:36]3[CH:44]=[CH:43][C:42]([CH:45]([CH3:47])[CH3:46])=[N:41][C:37]=3[N:38]=[CH:39][N:40]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 67040322HCID 67040322, compound

Product 1

HCID 67040920HCID 67040920, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The product from Example 172e was dissolved in a 1:1 mixture of TFA in DCM 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 (85 mg, 36%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.75 (d, J=6.99 Hz, 6 H), 7.21 (d, J=8.09 Hz, 2 H), 7.29-7.35 (m, 2 H), 7.38 (d, J=8.82 Hz, 1 H), 8.14 (d, J=8.82 Hz, 2 H), 8.25 (d, J=8.46 Hz, 1 H), 8.40 (d, J=8.46 Hz, 3 H), 8.56 (d, J=1.84 Hz, 1 H), 9.26 (s, 1 H), 9.37 (d, J=8.82 Hz, 1 H), 10.98 (s, 1 H); MS (ESI+) m/z 559 (M+TFA+H)+; (ESI−) m/z 557 (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 (85 mg, 36%)

Sources & evidence

ORD record
ord-ccef2662c90d42758925820118c8e70b
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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