Dimethylamine → HCID 24805090, compound

HRID 2245853Notes

Reaction equation

HRID 2245853 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]3[N:20]([CH:29]([CH3:31])[CH3:30])[C:21]([C:24](OCC)=[O:25])=[N:22][N:23]=3)=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:32]([F:35])([F:34])[F:33].[NH:36]([CH3:38])[CH3:37].CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]3[N:20]([CH:29]([CH3:31])[CH3:30])[C:21]([C:24]([N:36]([CH3:38])[CH3:37])=[O:25])=[N:22][N:23]=3)=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:32]([F:34])([F:33])[F:35]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 24804764HCID 24804764, compound

Product 1

HCID 24805090HCID 24805090, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a vial containing ethyl 5-(3-(4-chloro-3-(trifluoromethyl)benzenesulfonamido)-5-chloropyridin-2-yl)-4-isopropyl-4H-1,2,4-triazole-3-carboxylate (57 mg, 0.1 mmol) was added Me2NH in THF (1.0 mL of a 2.0M solution). The solution was stirred at room temperature for 16 h. EtOAc (30 mL) was added. The organic phase washed with water (2×10 mL) and dried over Na2SO4. The volatiles were removed in vacuo. The resulting residue was purified by preparative HPLC (20→95% gradient of MeCN—H2O with 0.1% TFA) and the pure fractions lyophilized to afford the title compound (3.7 mg, 7% yield). HPLC retention time=2.91 minutes. 1H NMR (400 MHz, CDCl3) δ 8.36 (d, J=2.0, 1H), 8.17 (d, J=2.4, 1H), 8.10 (d, J=2.4, 1H), 7.93 (dd, J=2.4, 8.4, 1H), 7.57 (d, J=8.4, 1H), 5.65 (sept, J=7.2, 1H), 3.20 (s, 3H), 3.12 (s, 3H), 1.52 (d, J=7.2, 6H). MS (ES) [M+H]+ expected 551.1, found 551.0.

Workup

  1. washThe organic phase washed with water (2×10 mL)
  2. dry with materialdried over Na2SO4
  3. customThe volatiles were removed in vacuo
  4. customThe resulting residue was purified by preparative HPLC (20→95% gradient of MeCN—H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-862612b4b64044268036e004522dc4bc
Source dataset
uspto-grants-2010_03
Patent number
US07683176B2

Reaction notes

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