Dimethylformamide → HCID 178509323, compound

HRID 2193475Notes

Reaction equation

HRID 2193475 reaction equation
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12].CCN=C=NCCCN(C)C.[CH:29]1[CH:30]=[CH:31][C:32]2[N:37](O)[N:36]=[N:35][C:33]=2[CH:34]=1.CN([CH:42]=[O:43])C>C(OCC)(=O)C>[NH2:1][C:2]1[S:10][C:5]2[CH2:6][N:7]([C:42]([C:29]3[CH:30]=[CH:31][C:32]4[NH:37][N:36]=[N:35][C:33]=4[CH:34]=3)=[O:43])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 43367333HCID 43367333, compound

Product 1

HCID 178509323HCID 178509323, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Starting material 12 (1.6 g, 6.4 mmol) was dissolved in 20 ml DMF. Then EDCI (1.46 g, 7.6 mmol) and HOBt (1.3 g, 9.5 mmol) were added. Now, one half of 1.04 g (6.4 mmol) 1H-1,2,3-benzothiazole-5-carboxyllic acid was added. The reaction mixture was stirred at ambient temperature over night. Then the other half of the 1H-1,2,3-benzothiazole-5-carboxyllic acid was added and the reaction mixture was again stirred at ambient temperature over night. The reaction mixture was now concentrated in vacuo yielding 7 g crude product. Those were taken up in ethyl acetate and water and the phases were separated. The organic phase was washed with water and the combined aqueous phases were washed with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The desired product 13 was isolated as a brown oil (1.2 g, 20% content, 10% yield).

Workup

  1. stirringthe reaction mixture was again stirred at ambient temperature over night
  2. concentrationThe reaction mixture was now concentrated in vacuo
  3. customyielding 7 g crude product
  4. customwater and the phases were separated
  5. washThe organic phase was washed with water
  6. washthe combined aqueous phases were washed with ethyl acetate
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f2743b9cbac4e5d86ca273124713747
Source dataset
uspto-grants-2012_12
Patent number
US08329907B2

Reaction notes

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