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

HRID 353931

반응식

HRID 353931 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-689434e9de3d4ffb8f1773c74edbc17b
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756372B2

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