Dimethylamine tetrahydrofuran → HCID 67350530, compound

HRID 1672798Notes

Reaction equation

HRID 1672798 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[N:27]=[C:26]([C:28](OC)=[O:29])[O:25][N:24]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:32]=1.[CH3:33][NH:34][CH3:35].C1COCC1>C1COCC1>[CH3:33][N:34]([CH3:35])[C:28]([C:26]1[O:25][N:24]=[C:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([N:14]3[CH2:13][C@H:12]4[N:8]([CH2:9][CH2:10][CH2:11]4)[C:7]4[N:32]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=4[C:15]3=[O:16])[CH:18]=2)[N:27]=1)=[O:29]

Participants

4

Reactant 2

HCID 22320367Dimethylamine tetrahydrofuranHCID 67349186HCID 67349186, compound

Product 1

HCID 67350530HCID 67350530, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (S)-3-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,2,4-oxadiazole-5-carboxylate (162 mg, 0.36 mmol) obtained in Step 1 of Example 80 was dissolved in THF (3.0 mL), and the mixture was stirred at room temperature for 2 hours after adding a 2.0 mol/L dimethylamine/THF solution (1.80 mL, 3.58 mmol). The residue obtained by concentrating the mixture under reduced pressure was then purified by silica gel column chromatography to give (S)—N,N-dimethyl 3-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,2,4-oxadiazole-5-carboxamide (151 mg, 90%).

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the mixture under reduced pressure
  3. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bc314cd3b0a7404390a0b3d41e701825
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

Loading…