Diisopropylcarbodiimide → HCID 10195903, compound

HRID 2109994Notes

Reaction equation

HRID 2109994 reaction equation
C(O[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([NH2:17])[C:11]=2[N:10]=[C:9]1[NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)[CH2:22][CH2:21]1)=[O:7])(C)(C)C.C(N=C=NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[C:57]([NH:60][CH2:61][CH2:62]C(O)=O)(=[O:59])[CH3:58].O1CCOCC1.Cl>O1CCCC1>[C:57]([NH:60][CH2:61][CH2:62][C:6]([NH:8][C:12]1[C:11]2[N:10]=[C:9]([NH:18][CH2:19][CH:20]3[CH2:21][CH2:22][N:23]([CH2:26][C:27]4[C:28]5[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:34]=[CH:35][CH:36]=4)[CH2:24][CH2:25]3)[NH:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)=[O:7])(=[O:59])[CH3:58]

Participants

7

Reactant 5

HCID 12734DiisopropylcarbodiimideHCID 76406N-Acetyl-beta-alanineHCID 27960291-Hydroxybenzotriazole hydrateHCID 204431481,4-Dioxane hydrochlorideHCID 69070294HCID 69070294, compound

Product 1

HCID 10195903HCID 10195903, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 4-amino-2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-amino]-benzimidazole-1-carboxylic acid tert-butyl ester (0.02 mmol) in tetrahydrofuran (1 ml), diisopropylcarbodiimide (0.05 mmol), 1-hydroxybenzotriazole monohydrate (0.05 mmol) and 3-acetylaminopropionic acid (0.05 mmol) were added and the mixture was stirred at room temperature overnight. After adding a 4N hydrogen chloride-1,4-dioxane solution (1 ml) to the reaction mixture, it was stirred at 50° C. for 1 hour, the solvent was removed under reduced pressure, and then dichloromethane and 5N aqueous sodium hydroxide were added to the obtained residue prior to stirring. The organic layer was passed through SCX (Bond Elute SCX500MG), and after washing the SCX with methanol, elution was performed with a 2N ammonia-methanol solution. The solvent was distilled off under reduced pressure to obtain 3-acetylamino-N-{2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-amino]-1H-benzimidazol-4-yl}-propionamide. The compound was identified by LC-MS.

Workup

  1. additionwere added
  2. stirringwas stirred at 50° C. for 1 hour
  3. customthe solvent was removed under reduced pressure
  4. additiondichloromethane and 5N aqueous sodium hydroxide were added to the obtained residue
  5. stirringto stirring
  6. washThe organic layer was passed through SCX (Bond Elute SCX500MG)
  7. washafter washing the SCX
  8. washwith methanol, elution
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0eb8d853a341444c9cce3c59d634fe03
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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