Diethylamine → HCID 57461518, compound

HRID 1663205Notes

Reaction equation

HRID 1663205 reaction equation
[CH:1]1([CH2:7][CH:8]([N:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:30])[CH:26]=3)[N:21]=[CH:20]2)[C:9]([NH:11][C:12]2[S:13][C:14]([CH:17]=O)=[CH:15][N:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:31]([CH2:34][CH3:35])[CH2:32][CH3:33].CC([O-])=O.[Na+].[BH3-]C#N.[Na+]>C(Cl)Cl.CO>[CH:1]1([CH2:7][CH:8]([N:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:30])[CH:26]=3)[N:21]=[CH:20]2)[C:9]([NH:11][C:12]2[S:13][C:14]([CH2:17][N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:15][N:16]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 57461517HCID 57461517, compound

Product 1

HCID 57461518HCID 57461518, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of Compound 150 (0.2 g, 0.4675 mmol), Et2NH (0.037 mL, 0.360 mmol), and NaOAc (46 mg, 0.561 mmol) was dissolved in DCM:MeOH (20:1, 1 mL) and stirred for 30 min. To this solution was added NaBH3CN (0.056 mg, 0.891 mmol) and the mixture was stirred at RT overnight. The reaction was quenched with aqueous NaHCO3 and extracted into DCM. The organic layer was washed with water and dried over MgSO4. The crude product was purified via preparative HPLC. 1H NMR (400 MHz, MeOD) δ ppm 0.99-1.27 (m, 6H) 1.35 (s, 6H) 1.59-1.89 (m, 5H) 2.06-2.16 (m, 1H) 2.17-2.28 (m, 1H) 3.21 (q, J=7.07 Hz, 4H) 4.59 (s, 2 H) 5.91 (dd, J=11.12, 5.56 Hz, 1H) 7.62-7.70 (m, 2H) 7.80 (dd, J=9.09, 4.80 Hz, 1H) 7.88 (dd, J=8.46, 2.91 Hz, 1H) 8.46 (s, 1H). [M+H] calc'd for C25H32FN5O2S, 486; found, 486.

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customThe reaction was quenched with aqueous NaHCO3
  3. extractionextracted into DCM
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customThe crude product was purified via preparative HPLC

Sources & evidence

ORD record
ord-62adc88ee89f42cb9f5a9430700374ac
Source dataset
uspto-grants-2011_10
Patent number
US08034822B2

Reaction notes

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