HCID 67040317, compound → HCID 67040441, compound

HRID 605236Notes

Reaction equation

HRID 605236 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][N: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:30])([F:32])[F:31])=[CH:25][N: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]([CH3:46])[CH3:47])=[N:41][C:37]=3[N:38]=[CH:39][N:40]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 67040317HCID 67040317, compound

Product 1

HCID 67040441HCID 67040441, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The product from Example 227d (366 mg, 0.555 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 (47 mg, 15%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.35 (d, J=6.99 Hz, 6 H), 3.29 (dt, J=13.70, 6.94 Hz, 1 H), 6.86-7.00 (m, 5 H), 7.88 (d, J=8.46 Hz, 1 H), 8.11 (dd, J=8.64, 2.39 Hz, 1 H), 8.21-8.30 (m, 2 H), 8.40 (d, J=8.82 Hz, 1 H), 8.79 (s, 1 H), 8.90 (s, 1 H), 9.00 (d, J=8.46 Hz, 1 H), 11.28 (s, 1 H); MS (ESI+) m/z 560 (M+TFA+H)+; (ESI−) m/z 558 (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 (47 mg, 15%)

Sources & evidence

ORD record
ord-b8af9099c1d9449693a42d02fc0a81c6
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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