Hydrochloric Acid → HCID 58124841, compound

HRID 1971687Notes

Reaction equation

HRID 1971687 reaction equation
[Br:1][C:2]1[C:3]([O:37][CH3:38])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:14]4[C:15](=[O:31])[N:16]([CH:28]([CH3:30])[CH3:29])[CH2:17][CH2:18][N:19](C(OC(C)(C)C)=O)[CH2:20][C:13]=4[C:12]([C:32]4[S:33][CH:34]=[CH:35][CH:36]=4)=[C:9]3[C:10]=2[CH:11]=1.C1(OC)C=CC=CC=1.CO.Cl>O1CCOCC1>[CH:28]([N:16]1[C:15](=[O:31])[C:14]2[N:8]3[CH2:7][CH2:6][C:5]4[CH:4]=[C:3]([O:37][CH3:38])[C:2]([Br:1])=[CH:11][C:10]=4[C:9]3=[C:12]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[C:13]=2[CH2:20][NH:19][CH2:18][CH2:17]1)([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7519AnisoleHCID 58124866HCID 58124866, compound

Product 1

HCID 58124841HCID 58124841, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 130 mg of 10l, 30 mg of anisole and 100 ul of methanol in 1 ml of dioxane was added 400 μl of 4N HCl in dioxane. The reaction mixture was stirred for 5 h and then quenched by addition of 10 ml of 5% aq. NaHCO3 and extracted with ethyl acetate. The organic layer was washed once with water, dried and concentrated. The residue was treated with diisopropyl ether, to afford 95 mg of 10u as white crystalline material; Mp 201-203° C.; Rf 0.20 (heptane-acetone 1/1). MS-ESI: [M+1] 499.94 and 501.95. NMR (CDCl3) 1.30 (d, 6, isoC3H7), 3.88 (s, 3, OCH3), 4.72 (m, 1, isoC3H7), 6.70, 7.18 (2×s, 2, Ar—H), 6.93, 7.13, 7.41 (3×m, 3, thiophene-H).

Workup

  1. customquenched by addition of 10 ml of 5% aq. NaHCO3
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed once with water
  4. customdried
  5. concentrationconcentrated
  6. additionThe residue was treated with diisopropyl ether

Sources & evidence

ORD record
ord-ba06d4f2cd884fe9b18d5c4d32c5f35d
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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