Dicyclohexylcarbodiimide → HCID 15342494, compound

HRID 341819

Reaction equation

HRID 341819 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH2:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[S:19][CH:18]=1.[C:26]([O:30][C:31]([NH:33][CH2:34][C:35](O)=[O:36])=[O:32])([CH3:29])([CH3:28])[CH3:27]>ClCCl>[C:26]([O:30][C:31](=[O:32])[NH:33][CH2:34][C:35]([NH:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[S:19][CH:18]=1)=[O:36])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 289923Thieno[2,3-b]pyridin-3-amine

Product 1

HCID 15342494HCID 15342494, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Dicyclohexylcarbodiimide (11 g) was added with stirring to a solution of 3-aminothieno[2,3-b]pyridine (8 g) and N-(tert-butoxycarbonyl)glycine (10 g) in 200 mL of dichloromethane. After one hour the reaction mixture was filtered to remove the separated 1,3-dicyclohexylurea and evaporated to an oil. Crystallization from ethyl ether afforded 14 g of a solid, m.p. 190°-192° C. Recrystallization of 3 g from acetonitrile afforded 2.4 g of crystals, m.p. 192°-194° C. Final recrystallization from acetonitrile afforded 2.0 g of crystals, m.p. 194°-196° C.

Workup

  1. filtrationAfter one hour the reaction mixture was filtered
  2. customto remove the separated 1,3-dicyclohexylurea
  3. customevaporated to an oil
  4. customCrystallization from ethyl ether

Sources & evidence

ORD record
ord-091f20146d8944a185bba925e92f47fe
Source dataset
uspto-grants-1999_01
Patent number
US05856335

Linked notes

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