Hydrochloric Acid → HCID 14601408, compound

HRID 2352283Notes

Reaction equation

HRID 2352283 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][O:9][CH3:10].[CH:11]([C:13]1[S:20][C:19]2[CH:18]=[C:17]([S:21]([NH2:24])(=[O:23])=[O:22])[S:16][C:15]=2[CH:14]=1)=O.C([BH3-])#N.[Na+].[BH4-].[Na+]>O>[CH3:2][O:3][CH2:4][CH2:5][N:6]([CH2:11][C:13]1[S:20][C:19]2[CH:18]=[C:17]([S:21]([NH2:24])(=[O:23])=[O:22])[S:16][C:15]=2[CH:14]=1)[CH2:7][CH2:8][O:9][CH3:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2383Bis(2-Methoxyethyl)amineHCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydrideHCID 14601401HCID 14601401, compound

Product 1

HCID 14601408HCID 14601408, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanolic HCl (2.7 mL of a 5.10M sol., 14 mmoles) was added to a solution of N,N-bis(2-methoxyethyl)amine. The solution was stirred for 15 minutes followed by the addition of 5-formylthieno[3,2-b]thiophene-2-sulfonamide (11) (0.742 g,. 3 mmole). The mixture was stirred at room temperature for 24 hours. Sodium cyanoborohydride (0.19 g., 3 mmoles) was added and the mixture was stirred for 24 hours. The mixture was cooled in ice water bath and sodium borohydride (0.38 g., 10 mmoles) was added in divided portions followed by stirring for 2 hours. The reaction was worked up by adding water (20 mL) and evaporating the methanol in vacuo to leave 1 g of crude product. The mixture was chromatographed on a 40×150 mm silica gel column eluting with 7% methanol in chloroform to give 0.66 g of 5-[N,N-bis(2-methoxyethyl)aminomethyl]thieno[3,2-b]thiophene-2-sulfonamide.

Workup

  1. stirringThe mixture was stirred at room temperature for 24 hours
  2. stirringthe mixture was stirred for 24 hours
  3. stirringby stirring for 2 hours
  4. customevaporating the methanol in vacuo
  5. customto leave 1 g of crude product
  6. customThe mixture was chromatographed on a 40×150 mm silica gel column
  7. washeluting with 7% methanol in chloroform

Sources & evidence

ORD record
ord-2edd5e7ad17140bf8f17a0b8bb9f4a36
Source dataset
uspto-grants-1989_10
Patent number
US04876271

Reaction notes

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