Tetrahydrofuran → HCID 59548471, compound

HRID 1622006Notes

Reaction equation

HRID 1622006 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1.F[C:17]1[C:22]([C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH2:30])[N:24]=2)=[CH:21][CH:20]=[CH:19][N:18]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1.[NH4+].[Cl-]>CN(C=O)C>[NH2:30][C:25]1[N:26]=[C:27]([CH3:29])[N:28]=[C:23]([C:22]2[C:17]([NH:1][C:2]3[CH:3]=[C:4]([NH:9][S:10]([CH:13]4[CH2:15][CH2:14]4)(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)[N:24]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 665998524-(2-Fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amineHCID 71480921HCID 71480921, compound

Product 1

HCID 59548471HCID 59548471, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a 15 mL RB flask was added N-(5-amino-2-chloropyridin-3-yl)cyclopropanesulfonamide (0.050 g, 0.202 mmol), 4-(2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.050 g, 0.242 mmol), and DMF (2.0 mL). The mixture was cooled to 0° C. under N2. Sodium bis(trimethylsilyl)amide, 1.0 m solution in THF (Aldrich) (0.807 mL, 0.807 mmol) was then added to the solution in one portion. The now burgundy color mixture was stirred at 0° C. for 10 min then warmed up to rt for 30 min. The reaction mixture was poured into the beaker which had filled with 15 mL sat. NH4Cl. The resulting mixture was stirred at rt for 15 h. The ppt in the solution mixture was collected by filtration. The solid was rinsed with water and dried opened to the air for 4 h. This crude product was purified by column chromatography (40 g, 3% MeOH in DCM) to afford the desired product as a yellow solid (60.0 mg). MS (ESI pos. ion) m/z: 433.0. 1H NMR (300 MHz, CDCl3) δ ppm 0.97-1.14 (m, 2H) 1.33 (dd, J=4.60, 1.83 Hz, 2H) 2.51-2.69 (m, 4H) 5.42 (br. s., 2H) 6.75 (s, 1H) 6.92 (dd, J=7.82, 4.90 Hz, 1H) 8.32-8.45 (m, 1H) 8.56 (d, J=2.34 Hz, 1H) 8.76 (d, J=2.34 Hz, 1H) 8.87 (dd, J=7.89, 1.75 Hz, 1H) 12.36 (s, 1H).

Workup

  1. temperaturethen warmed up to rt for 30 min
  2. additionThe reaction mixture was poured into the beaker which
  3. stirringThe resulting mixture was stirred at rt for 15 h
  4. filtrationThe ppt in the solution mixture was collected by filtration
  5. washThe solid was rinsed with water
  6. customdried
  7. waitopened to the air for 4 h
  8. customThis crude product was purified by column chromatography (40 g, 3% MeOH in DCM)

Sources & evidence

ORD record
ord-1a0ab054c2284692ac5ddefca0ddc097
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

Loading…