HCID 67040207, compound → HCID 67041094, compound

HRID 605278Notes

Reaction equation

HRID 605278 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][C:26]([Br:29])=[CH:27][CH:28]=3)=[O:23])=[CH:17][C:16]=2[NH:30][C:31]2[C:32]3[CH:40]=[CH:39][C:38]([CH:41]([CH3:43])[CH3:42])=[N:37][C:33]=3[N:34]=[CH:35][N:36]=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][C:26]([Br:29])=[CH:27][CH:28]=3)=[O:23])=[CH:17][C:16]=2[NH:30][C:31]2[C:32]3[CH:40]=[CH:39][C:38]([CH:41]([CH3:42])[CH3:43])=[N:37][C:33]=3[N:34]=[CH:35][N:36]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 67040207HCID 67040207, compound

Product 1

HCID 67041094HCID 67041094, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The product from Example 257c (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 (16 mg, 6%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.32 (t, J=6.99 Hz, 6 H), 3.18-3.33 (m, 1 H), 6.82-6.91 (m, 4 H), 6.99 (d, J=9.19 Hz, 1 H), 7.39 (d, J=4.04 Hz, 1 H), 7.61 (dd, J=8.82, 2.57 Hz, 1 H), 7.81 (d, J=8.46 Hz, 1 H), 7.86 (d, J=4.04 Hz, 1 H), 7.99 (d, J=2.57 Hz, 1 H), 8.81 (s, 1 H), 8.91 (d, J=8.09 Hz, 1 H), 10.45 (s, 1 H); MS (ESI+) m/z 575 (M+TFA+H)+; (ESI−) m/z 573 (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 (16 mg, 6%)

Sources & evidence

ORD record
ord-0085645fba0849669ed1264c0b148201
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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