Dimethylformamide → 2-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid-[1-benzyl-2-methoxy-2-(methoxymethyl-carbamoyl)-ethyl]-amide

HRID 1612046Notes

Reaction equation

HRID 1612046 reaction equation
C(N(CC)CC)C.[NH2:8][CH:9]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:10]([O:17][CH3:18])[C:11]([N:13](OC)[CH3:14])=[O:12].[Cl:26][C:27]1[S:37][C:30]2[NH:31][C:32]([C:34](O)=[O:35])=[CH:33][C:29]=2[CH:28]=1.C1C=CC2N(O)N=NC=2C=1.CN([CH:51]=[O:52])C>C(OCC)(=O)C>[CH2:19]([CH:9]([NH:8][C:34]([C:32]1[NH:31][C:30]2[S:37][C:27]([Cl:26])=[CH:28][C:29]=2[CH:33]=1)=[O:35])[CH:10]([O:17][CH3:18])[C:11](=[O:12])[NH:13][CH2:14][O:52][CH3:51])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 104428202-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acidHCID 222529473-amino-2,N-dimethoxy-N-methyl-4-phenyl-butyramide

Product 1

HCID 222529512-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid-[1-benzyl-2-methoxy-2-(methoxymethyl-carbamoyl)-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine was added dropwise to a solution of 3-amino-2,N-dimethoxy-N-methyl-4-phenyl-butyramide (PCT International Application Publication No. WO 96/39385) (1.65 g, 5.71 mmol) in DMF (15 mL) and cooled in an ice bath. A solution of 2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid (U.S. Pat. No. 6,399,601) (1.1 g, 5.71 mmol) in 15 mL of DMF was added dropwise followed by the addition of HOBT (1.16 g, 11.4 mmol) neat. The reaction mixture was stirred for 5 min and N-ethyliminomethylene-N,N′-dimethyl-propane-1,3-diamine (1.10 g, 5.71 mmol) was added neat. The resulting mixture was stirred at room temperature for 18 hrs. The reaction mixture was diluted with ethyl acetate (150 mL) and washed with saturated ammonium chloride, water, and brine. The ethyl acetate was dried and evaporated in vacuo to yield 2.54 g of crude product. Chromatography over silica gel, eluting with ethyl acetate/hexanes (1:2), afforded 1.43 g of the title compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 18 hrs
  2. washwashed with saturated ammonium chloride, water, and brine
  3. dry with materialThe ethyl acetate was dried
  4. customevaporated in vacuo
  5. customto yield 2.54 g of crude product
  6. washChromatography over silica gel, eluting with ethyl acetate/hexanes (1:2)

Sources & evidence

ORD record
ord-9c08440f20d54915aa9e7039f4f49833
Source dataset
uspto-grants-2006_01
Patent number
US06992101B2

Reaction notes

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