Dimethylformamide → HCID 70656360, compound

HRID 872588Notes

Reaction equation

HRID 872588 reaction equation
[C:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([NH:11][C@@H:12]([CH3:28])[CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21](Cl)[CH:20]=3)=[N:15]2)=[O:10])[CH:5]=1)(=[O:3])[CH3:2].CN(C=O)C.[CH3:34][S-:35].[Na+]>CC#N>[C:1]([C:4]1[CH:5]=[C:6]([C:9]([NH:11][C@@H:12]([CH3:28])[CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([S:35][CH3:34])[CH:20]=3)=[N:15]2)=[O:10])[NH:7][N:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolate2×HCID 178466824HCID 178466824, compound

Product 1

HCID 70656360HCID 70656360, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

(S)—5-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-3-carboxamide (64 mg, 0.16 mmol) was placed into a microwave vial. DMF (1 ml) and sodium thiomethoxide (12.4 mg, 0.18 mmol) were added and the reaction mixture was heated in microwave reactor at 150° C. Sodium thiomethoxide was added after 30, 30 and 20 min of heating (12.4 mg, 5.6 mg and 5.6 mg, respectively). After total of 90 min of heating DMF was evaporated, and the evaporation residual was taken up in DCM and washed with water. Organic phase was dried over Na2SO4, filtered and evaporated. Thus obtained crude product was suspended in MeCN. Suspension was filtered to give 9 mg (14%) of the title compound as a colourless solid. Filtrate was purified by CombiFlash (column: C-18 silica, eluent: 0-100% MeCN in water) to yield 13 mg (20%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.11-1.20 (m, 3H), 2.49 (s, 3H, overlap with DMSO) 2.57-2.64 (m, 3H), 4.20-4.55 (m, 3H), 6.91 (s, 1H), 7.31 (s, 1H), 7.62-7.89 (m, 4H), 8.47 (dd, 1H), 14.2 (d, 1H).

Workup

  1. temperatureof heating (12.4 mg, 5.6 mg and 5.6 mg
  2. customAfter total of 90 min of heating DMF was evaporated
  3. washwashed with water
  4. dry with materialOrganic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThus obtained crude product
  8. filtrationSuspension was filtered

Sources & evidence

ORD record
ord-b453a54ebf524f7d8b34b012c4db6dbb
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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