Thiophene → cis-4-amino-5-chloro-N-[1-(3,3-dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)-3-methoxy-4-piperidinyl]-2-methoxybenzamide

HRID 1110400

반응식

HRID 1110400 반응식
[CH3:1][C:2]1([CH3:14])[CH2:7][O:6][C:5]2([CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[O:4][CH2:3]1.[NH2:15][C:16]1[C:32]([Cl:33])=[CH:31][C:19]([C:20]([NH:22][C@H:23]2[CH2:28][CH2:27][NH:26][CH2:25][C@H:24]2[O:29][CH3:30])=[O:21])=[C:18]([O:34][CH3:35])[CH:17]=1.S1C=CC=C1.[H][H]>CO.[Pt]>[NH2:15][C:16]1[C:32]([Cl:33])=[CH:31][C:19]([C:20]([NH:22][C@H:23]2[CH2:28][CH2:27][N:26]([CH:10]3[CH2:11][CH2:12][C:5]4([O:6][CH2:7][C:2]([CH3:14])([CH3:1])[CH2:3][O:4]4)[CH2:8][CH2:9]3)[CH2:25][C@H:24]2[O:29][CH3:30])=[O:21])=[C:18]([O:34][CH3:35])[CH:17]=1

참가 물질

7

반응물 4

HCID 8030ThiopheneHCID 5879683,3-Dimethyl-1,5-dioxaspiro(5.5)undecan-9-oneHCID 98616214-Amino-5-chloro-2-methoxy-N-[(3R,4S)-3-methoxypiperidin-4-YL]benzamideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67922714cis-4-amino-5-chloro-N-[1-(3,3-dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)-3-methoxy-4-piperidinyl]-2-methoxybenzamide수율 62.6%

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 887Methanol용매2회

실험 절차

A mixture of 10 parts of 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-one, 9.42 parts of cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4piperidinyl)benzamide, 1 part of a solution of thiophene in methanol 4% and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried in vacuo at 60° C., yielding 9.33 parts (62.6%) of cis-4-amino-5-chloro-N-[1-(3,3-dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)-3-methoxy-4-piperidinyl]-2-methoxybenzamide; mp. 187.5° C. (compound 92).

후처리

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from acetonitrile
  4. filtrationThe product was filtered off
  5. customdried in vacuo at 60° C.

출처 및 근거

ORD 기록
ord-7bad57b174584436af069fcf2bf39984
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04975439

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