Triethylamine → HCID 58529530, compound

HRID 1972900Notes

Reaction equation

HRID 1972900 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][N:34]([CH3:39])[S:35](Cl)(=[O:37])=[O:36].C(N(CC)CC)C>C1(C)C=CC=CC=1>[NH2:26][C:24]1[C:25]2=[C:17]([C:12]3[CH:13]=[CH:14][C:15]4[C:10]([CH:11]=3)=[N:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:16]=4)[CH:18]=[C:19]([CH:27]3[CH2:32][CH2:31][N:30]([S:35]([N:34]([CH3:39])[CH3:33])(=[O:37])=[O:36])[CH2:29][CH2:28]3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 83372Dimethylsulphamoyl chloride2×HCID 16066662HCID 16066662, compound

Product 1

HCID 58529530HCID 58529530, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 5-(2-benzyl-2H-indazol-6-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (80 mg, 0.17 mmol) in toluene (1 mL) was added N,N-dimethylsulfamoyl chloride (27 mg, 0.19 mmol) and triethylamine (73 μL, 0.52 mmol). The reaction was stirred at rt for 17 h. Additional N,N-dimethylsulfamoyl chloride (27 mg, 0.19 mmol) and triethylamine (73 μL, 0.52 mmol) were added and the reaction continued to stir at rt for 6 h. The mixture was partitioned between EtOAc (20 mL) and H2O (20 mL). The layers were separated and the organic phase was washed with saturated, aqueous NaHCO3 (20 mL), brine, dried (Na2SO4) and concentrated. The resulting solid was triturated with Et2O and was collected by vacuum filtration to afford 92 mg (99%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.55 (s, 1 H), 7.90 (s, 1 H), 7.80 (d, 1 H), 7.59 (s, 1 H), 7.28-7.37 (m, 5 H), 7.14 (d, 1 H), 6.63 (s, 1 H), 5.65 (s, 2 H), 3.67 (d, 2 H), 3.22-3.33 (m, 1 H), 3.01 (t, 2 H), 2.77 (s, 6 H), 2.07 (d, 2 H), 1.62-1.77 (m, 2 H); ES-MS m/z 531.26 [M+H]+, HPLC RT (min) 2.75.

Workup

  1. stirringto stir at rt for 6 h
  2. customThe mixture was partitioned between EtOAc (20 mL) and H2O (20 mL)
  3. customThe layers were separated
  4. washthe organic phase was washed with saturated, aqueous NaHCO3 (20 mL), brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe resulting solid was triturated with Et2O
  8. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-40a29aad35c14b8dbb29cbf56a0558b2
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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