Methylamine → HCID 178482370, compound

HRID 2402446Notes

Reaction equation

HRID 2402446 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:29]#[N:30])=[C:11]([C:19]2[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=2)[S:12][C:13]=1[C:14]1[NH:18][CH:17]=[N:16][N:15]=1.O1CCCC1.[CH3:36][NH2:37]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:29]#[N:30])=[C:11]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:37][CH3:36])[N:20]=2)[S:12][C:13]=1[C:14]1[NH:18][CH:17]=[N:16][N:15]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 178504846HCID 178504846, compound

Product 1

HCID 178482370HCID 178482370, compoundYield 81%

Procedure

4-(2,4-dichlorophenyl)-2-[2-(methylsulfonyl)pyrimidin-4-yl]-5-(4H-1,2,4-triazol-3-yl)thiophene-3-carbonitrile (0.047 g, 0.10 mmol) was dissolved in 2.0 M of Methylamine in Tetrahydrofuran (1.74 mL, 0.00349 mol) and the mixture was stirred at room temperature for 1 hour. The solvent was concentrated in vacuo and the residue was purified using ISCO chromatography on silica gel, elution 30% ethyl acetate in hexanes to ethyl acetate to afford the title compound (0.037 g, 81%). LCMS: (FA) ES+, 428, 430. 1H NMR (400 MHz, d4-methanol) δ: 8.07-8.01 (m, 1H), 7.99 (s, 1H), 7.24-7.21 (m, 1H), 7.09-7.02 (m, 2H), 6.97 (d, J=5.04 Hz, 1H), 2.62 (s, 3H).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe residue was purified
  3. washon silica gel, elution 30% ethyl acetate in hexanes to ethyl acetate

Sources & evidence

ORD record
ord-9c9e124b7f7a402bb63ba4f7ea6b679e
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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