Trifluoroacetic acid → HCID 11168089, compound

HRID 2219078Notes

Reaction equation

HRID 2219078 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=2)=[CH:5][CH:4]=1.N[NH:24][C:25]([NH2:27])=[S:26].[C:28]([OH:34])([C:30](F)(F)F)=O>>[NH2:10][C:9]1[CH:6]=[CH:5][CH:4]=[CH:3][C:30]=1[C:28](=[O:34])[CH2:12][CH2:13][NH:14][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:12]([C:13]3[S:26][C:25]([NH2:27])=[N:24][N:14]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2723789ThiosemicarbazideHCID 68809004HCID 68809004, compound

Product 1

HCID 11168089HCID 11168089, compound

Conditions

Temperature
60 °C

Procedure

A mixture of the nitrile (0.014 g, 0.032 g) and thiosemicarbazide (0.004 g, 0.049 mmol) in TFA was heated to 60° C. for 15 hr. The mixture was then cooled and concentrated. The residue was taken up in DMF and purified by reverse phase HPLC (5% CH3CN:95% H2O:0.01% TFA to 95% CH3CN: 5% H2O: 0.01% TFA). NMR (500 MHz, d6 DMSO) δ 12.98 (bs, 1H), 8.77 (bs, 2H), 8.08 (d, 1H, J=2.19 Hz), 7.95 (d, 2H, J=7.1 Hz), 7.70 (d, 1H, J=6.84 Hz), 7.67-7.60 (m, 3H), 7.50 (t, 2H, J=7.81 Hz) 7.38-7.25 (m, 7H), 6.79 (d, 1H, J=7.6 Hz), 6.57 (t, 1H, J=8.05 Hz), 4.22 (t, 2H, J=5.61 Hz), 3.39 (t, 2H, J=6.8 Hz), 3.28-3.15 (m, 2H) LRMS m/z (M+H) Calcd: 507.0, found: 507.0

Workup

  1. temperatureThe mixture was then cooled
  2. concentrationconcentrated
  3. custompurified by reverse phase HPLC (5% CH3CN:95% H2O:0.01% TFA to 95% CH3CN: 5% H2O: 0.01% TFA)

Sources & evidence

ORD record
ord-acf10137eee14d8dbebcec7c1734bc82
Source dataset
uspto-grants-2008_08
Patent number
US07414055B2

Reaction notes

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