1,2-Dichloroethane → 4-Acetylamino-N-[1-(4-cyano-tetrahydro-pyran-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-benzamide

HRID 353931

Reaction equation

HRID 353931 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[C:29]([C:31]1([NH:37][C:38]([CH:40]([NH2:48])[CH2:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:39])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)#[N:30]>CN(C=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:48][CH:40]([C:38](=[O:39])[NH:37][C:31]2([C:29]#[N:30])[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)[CH2:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:11])=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 19266p-Acetamidobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 22063105[1-(4-Cyano-tetrahydro-pyran-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-amine hydrochloride

Product 1

HCID 694202734-Acetylamino-N-[1-(4-cyano-tetrahydro-pyran-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-benzamideYield 28.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Acetamidobenzoic acid (353 mg, 1.98 mmol), EDC (378 mg, 1.98 mmol), and HOBT (268 mg, 1.98 mmol) were combined in 15 mL of DMF and stirred for 20 min. Solid [1-(4-cyano-tetrahydro-pyran-4-ylcarbamoyl)-2-cyclohexyl-ethyl]-amine hydrochloride (625 mg, 1.98 mmol) was added. The reaction was stirred for 16 hours. The volatiles were removed with a pump and the resulting residue was triturated, with rapid stirring, with 250 mL of saturated aqueous sodium bicarbonate. The resulting solid was collected by filtration and washed with 250 mL of water. The solid was dried in vacuo to give the title compound (250 mg); MS, m/z 441=M+1.

Workup

  1. stirringThe reaction was stirred for 16 hours
  2. customThe volatiles were removed with a pump
  3. customthe resulting residue was triturated, with rapid stirring, with 250 mL of saturated aqueous sodium bicarbonate
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with 250 mL of water
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-689434e9de3d4ffb8f1773c74edbc17b
Source dataset
uspto-grants-2004_06
Patent number
US06756372B2

Linked notes

Loading…