Dimethylformamide → HCID 68482341, compound

HRID 1523673Notes

Reaction equation

HRID 1523673 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:4][CH2:3][C@@H:2]1[C:11]1[N:15]=[C:14]([NH:16][C:17]2[N:22]=[CH:21][C:20]([S:23]CCC(OC)=O)=[CH:19][C:18]=2[O:30][C:31]2[C:32]([CH3:38])=[N:33][N:34]([CH3:37])[C:35]=2[CH3:36])[S:13][N:12]=1.CC([O-])(C)C.[K+].Br[CH2:46][CH2:47][O:48][CH3:49].CN(C=O)C>C1COCC1>[CH3:49][O:48][CH2:47][CH2:46][S:23][C:20]1[CH:19]=[C:18]([O:30][C:31]2[C:32]([CH3:38])=[N:33][N:34]([CH3:37])[C:35]=2[CH3:36])[C:17]([NH:16][C:14]2[S:13][N:12]=[C:11]([C@H:2]3[CH2:3][O:4][C:5]4([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]4)[O:1]3)[N:15]=2)=[N:22][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 809722-Bromoethyl methyl etherHCID 23665647Potassium tert-butoxideHCID 68480265HCID 68480265, compound

Product 1

HCID 68482341HCID 68482341, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-methyl 3-(6-(3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-ylamino)-5-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-3-ylthio)propanoate (0.420 g, 0.749 mmol) in THF (10 mL) was added potassium 2-methylpropan-2-olate (2.36 ml, 2.36 mmol) and the reaction was stirred at ambient temperature for 5 minutes. 1-Bromo-2-methoxyethane (0.132 g, 0.899 mmol) (as a solution in 2 mL THF) and DMF (1 mL) were added and the reaction was stirred for 20 minutes at ambient temperature. The solution was quenched with water, extracted with CH2Cl2, dried over sodium sulfate, filtered and concentrated. The residue was purified over silica gel (100% EtOAc) to afford (S)—N-(5-(2-methoxyethylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-amine (0.200 g, 50.1% yield).

Workup

  1. stirringthe reaction was stirred for 20 minutes at ambient temperature
  2. customThe solution was quenched with water
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified over silica gel (100% EtOAc)

Sources & evidence

ORD record
ord-e35369c64ad54bfc901f1d444d4d29b9
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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