Dimethyl Sulfide → HCID 58882981, compound

HRID 2364134Notes

Reaction equation

HRID 2364134 reaction equation
S(C)C.[NH2:4][C:5]1[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:7][CH:8]=[C:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1.[CH3:23][S:24]([C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1)(=[O:26])=[O:25]>C(Cl)Cl.CC(O)=O>[CH2:11]([C:9]1[CH:10]=[C:5]([NH:4][CH2:31][C:30]2[CH:29]=[CH:28][C:27]([S:24]([CH3:23])(=[O:26])=[O:25])=[CH:34][CH:33]=2)[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:7][CH:8]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 1068Dimethyl Sulfide2×HCID 2203764-(Methylsulfonyl)benzaldehyde2×HCID 42637771HCID 42637771, compound

Product 1

HCID 58882981HCID 58882981, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1M BH3.SMe2 in CH2Cl2 (7 mL, 7 mmol) was added dropwise to a solution of ethyl 3-amino-5-benzylpyridine-2-carboxylate (600 mg, 2.34 mmol) and 4-methylsulfonyl benzaldehyde (647 mg, 3.51 mmol) in CH2Cl2 (8 mL) and HOAc (4 mL). The mixture was stirred at rt for 30 min and additional amounts of 1M BH3.SMe2 (2 mL, 2 mmol) and 4-methylsulfonyl benzaldehyde (160 mg, 3.51 mmol) were added. After stirring overnight at rt, the solution was concentrated in vacuo, dissolved in CH2Cl2 and washed with NaHCO3 solution. The organic layer was dried, concentrated and chromatographed on silica gel eluting with 0-5% MeOH/CH2Cl2. This afforded the product as an amber foam: 1H NMR (CDCl3) δ 8.31 (1H, br m), 7.97 (1H, s), 7.86 (2H, d, J=8 Hz), 7.42 (2H, d, J=8 Hz), 7.22 (3H, m), 7.02 (2H, dd, J=8, 2 Hz), 6.58 (1H, s), 4.46 (2H, br), 4.46 (2H, q, J=7 Hz), 3.87 (2H, s), 3.04 (3H, s), 1.45 (3H, t, J=7 Hz); HRMS calcd for C23H24N2O4S+H+: 425.1535. Found: 425.1524.

Workup

  1. stirringAfter stirring overnight at rt
  2. concentrationthe solution was concentrated in vacuo
  3. dissolutiondissolved in CH2Cl2
  4. washwashed with NaHCO3 solution
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customchromatographed on silica gel eluting with 0-5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-b41c5afed04140969b5a6a3ecc74b2dd
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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