1-Hydroxybenzotriazole → HCID 18723325, compound

HRID 1909010Notes

Reaction equation

HRID 1909010 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(O[C:40]([N:42]1[CH2:47][CH2:46][CH:45]([NH2:48])[CH2:44][CH2:43]1)=O)(C)(C)C.CCN(C(C)C)C(C)C>ClCCl>[CH3:40][N:42]1[CH2:47][CH2:46][CH:45]([NH:48][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[N:1]=[CH:2][NH:3][C:4]=3[CH:9]=2)=[O:12])[CH2:44][CH2:43]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4594565-Benzimidazolecarboxylic acidHCID 12682914-Amino-1-Boc-piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18723325HCID 18723325, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 1 (Amide Coupling): 5-Benzimidazole carboxylic acid (0.50 g, 3.1 mmol), EDC.HCl (0.72 g, 3.7 mmol) and HOBt (0.58 mg, 3.7 mmol) in dichloromethane (11 mL) was stirred at room temperature for 10 minutes. 4-Amino-piperidine-1-carboxylic acid tert-butyl ester (0.70 g, 3.4 mmol) and DIPEA (0.59 ml, 3.4 mmol) were added and the mixture was stirred for 3 hours. The mixture was then partitioned between EtOAc and sat. aqueous Na2CO3. The layers were separated and the aqueous layer was extracted with EtOAc (×3). The combined organic layers were washed with water, brine and dried (MgSO4). The solvent was evaporated in vacuo to give 3H-benzoimidazole-5-carboxylic acid (1-methyl-piperidin-4-yl)-amide.

Workup

  1. customThe mixture was then partitioned between EtOAc and sat. aqueous Na2CO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (×3)
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1fd81b26925745fc8aed82d594e779a6
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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