Carbon Tetrachloride → HCID 178474070, compound

HRID 2282145Notes

Reaction equation

HRID 2282145 reaction equation
[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])=[C:6]([C:16]2[NH:20][CH:19]=[N:18][N:17]=2)[S:5][C:4]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28](=[O:30])[CH3:29])[CH:22]=1)#[N:2].[Br:31]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl.C(#N)C>>[Br:31][C:19]1[NH:20][C:16]([C:6]2[S:5][C:4]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28](=[O:30])[CH3:29])[CH:22]=3)=[C:3]([C:1]#[N:2])[C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])=[N:17][N:18]=1

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 178474071HCID 178474071, compound

Product 1

HCID 178474070HCID 178474070, compoundYield 80.4%

Conditions

Temperature
85 °C

Procedure

A suspension of N-(4-(3-cyano-4-(2,4-dichlorophenyl)-5-(4H-1,2,4-triazol-3-yl)thiophen-2-yl)pyridin-2-yl)acetamide (0.0700 g, 0.154 mmol) and N-Bromosuccinimide (33.1 mg, 0.186 mmol) in Carbon tetrachloride (2.5 mL, 26 mmol) was heated to 85° C. in a capped vial for 2.5 hours. To the suspension was added dry Acetonitrile (6.0 mL, 110 mmol) and the mixture was heated at 85° C. (turned into a clear solution) for additional 2 hours. The mixture was cooled to r.t., evaporated in rotavapor. The residue was dry loaded in a silica column and eluted with MeOH/DCM (0/100 to 5/95) to give a solid product (66.0 mg, yield 80.4%). LCMS: (FA) ES+, 533, 535, 537 and ES− 531, 533, 535. 1H NMR (400 MHz, d1-chloroform) δ: 8.65 (s, 1H), 8.42 (d, J=5.02 Hz, 1H), 8.26 (s, 1H), 7.61 (d, J=2.01 Hz, 1H), 7.56 (dd, J=5.27, 1.76 Hz, 1H), 7.43-7.45 (dd, J=8.28, 2.01 Hz, 1H), 7.37-7.39 (d, J=8.28 Hz, 1H), 2.26 (s, 3H).

Workup

  1. temperaturethe mixture was heated at 85° C. (
  2. customfor additional 2 hours
  3. temperatureThe mixture was cooled to r.t.
  4. customevaporated in rotavapor
  5. customThe residue was dry
  6. washeluted with MeOH/DCM (0/100 to 5/95)

Sources & evidence

ORD record
ord-8311799d389140cbbb3213736fe266ff
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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