Acetyl chloride → N-[5-(8-acetyl-1-thia-3,8-diazaspiro[4.5]deca-2-en-2-yl)-2-methyl-4H-thieno[3,2-b]pyrrol-3-yl]-N-methylthiophene-2-sulfonamide

HRID 453590Notes

Reaction equation

HRID 453590 reaction equation
[CH3:1][N:2]([C:11]1[C:15]2[NH:16][C:17]([C:19]3[S:20][C:21]4([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH2:22][N:23]=3)=[CH:18][C:14]=2[S:13][C:12]=1[CH3:29])[S:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)(=[O:5])=[O:4].C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>O1CCCC1>[C:37]([N:26]1[CH2:27][CH2:28][C:21]2([S:20][C:19]([C:17]3[NH:16][C:15]4[C:11]([N:2]([CH3:1])[S:3]([C:6]5[S:7][CH:8]=[CH:9][CH:10]=5)(=[O:5])=[O:4])=[C:12]([CH3:29])[S:13][C:14]=4[CH:18]=3)=[N:23][CH2:22]2)[CH2:24][CH2:25]1)(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59411372N-methyl-N-[2-methyl-5-(1-thia-3,8-diazaspiro[4.5]deca-2-en-2-yl)-4H-thieno[3,2-b]pyrrol-3-yl]thiophene-2-sulfonamide

Product 1

HCID 24880660N-[5-(8-acetyl-1-thia-3,8-diazaspiro[4.5]deca-2-en-2-yl)-2-methyl-4H-thieno[3,2-b]pyrrol-3-yl]-N-methylthiophene-2-sulfonamideYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-methyl-N-[2-methyl-5-(1-thia-3,8-diazaspiro[4.5]deca-2-en-2-yl)-4H-thieno[3,2-b]pyrrol-3-yl]thiophene-2-sulfonamide (180 mg), triethylamine (78 μL) and tetrahydrofuran (5 mL) was added acetyl chloride (32 μL), and the mixture was stirred at room temperature for 10 min. The reaction mixture was concentrated, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to give N-[5-(8-acetyl-1-thia-3,8-diazaspiro[4.5]deca-2-en-2-yl)-2-methyl-4H-thieno[3,2-b]pyrrol-3-yl]-N-methylthiophene-2-sulfonamide (115 mg, yield 57%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). melting point 231° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1N hydrochloric acid was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1e625066b94a434bb6486e696831462f
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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