Hydrochloric Acid → (2R,6S,7R,9R,13aS,14aR,16aS,Z)-6-amino-N-(1-(fluoromethyl)cyclopropylsulfonyl)-2-(2-(4-isopropoxyphenyl)-7-methoxyquinolin-4-yloxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxamide hydrochloride

HRID 1852196노트

반응식

HRID 1852196 반응식
[F:1][CH2:2][C:3]1([S:6]([NH:9][C:10]([C@@:12]23[CH2:27][C@H:26]2[CH:25]=[CH:24][CH2:23][CH2:22][CH:21]([CH3:28])[CH2:20][C@@H:19]([CH3:29])[C@H:18]([NH:30]C(=O)OC(C)(C)C)[C:17](=[O:38])[N:16]2[CH2:39][C@H:40]([O:42][C:43]4[C:52]5[C:47](=[CH:48][C:49]([O:53][CH3:54])=[CH:50][CH:51]=5)[N:46]=[C:45]([C:55]5[CH:60]=[CH:59][C:58]([O:61][CH:62]([CH3:64])[CH3:63])=[CH:57][CH:56]=5)[CH:44]=4)[CH2:41][C@H:15]2[C:14](=[O:65])[NH:13]3)=[O:11])(=[O:8])=[O:7])[CH2:5][CH2:4]1.[ClH:66]>O1CCOCC1>[ClH:66].[NH2:30][C@@H:18]1[C:17](=[O:38])[N:16]2[CH2:39][C@H:40]([O:42][C:43]3[C:52]4[C:47](=[CH:48][C:49]([O:53][CH3:54])=[CH:50][CH:51]=4)[N:46]=[C:45]([C:55]4[CH:60]=[CH:59][C:58]([O:61][CH:62]([CH3:64])[CH3:63])=[CH:57][CH:56]=4)[CH:44]=3)[CH2:41][C@H:15]2[C:14](=[O:65])[NH:13][C@:12]2([C:10]([NH:9][S:6]([C:3]3([CH2:2][F:1])[CH2:4][CH2:5]3)(=[O:7])=[O:8])=[O:11])[CH2:27][C@H:26]2[CH:25]=[CH:24][CH2:23][CH2:22][C@@H:21]([CH3:28])[CH2:20][C@H:19]1[CH3:29]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86683252tert-butyl (2R,6S,7R,13aS,14aR,16aS,Z)-14a-(1-(fluoromethyl)cyclopropylsulfonylcarbamoyl)-2-(2-(4-isopropoxyphenyl)-7-methoxyquinolin-4-yloxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-ylcarbamate

생성물 1

HCID 86683253(2R,6S,7R,9R,13aS,14aR,16aS,Z)-6-amino-N-(1-(fluoromethyl)cyclopropylsulfonyl)-2-(2-(4-isopropoxyphenyl)-7-methoxyquinolin-4-yloxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxamide hydrochloride수율 90%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of tert-butyl (2R,6S,7R,13aS,14aR,16aS,Z)-14a-(1-(fluoromethyl)cyclopropylsulfonylcarbamoyl)-2-(2-(4-isopropoxyphenyl)-7-methoxyquinolin-4-yloxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-ylcarbamate (130 mg, 0.14 mmole) was added to a solution of HCl in dioxane (4N, 5 mL) and the solution was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure to get crude compound. The crude compound was washed with diethyl ether to afford (2R,6S,7R,9R,13aS,14aR,16aS,Z)-6-amino-N-(1-(fluoromethyl)cyclopropylsulfonyl)-2-(2-(4-isopropoxyphenyl)-7-methoxyquinolin-4-yloxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxamide hydrochloride (100 mg, 90%) as off-white solid. MS: MS m/z 821.3 (M++1).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customto get crude compound
  3. washThe crude compound was washed with diethyl ether

출처 및 근거

ORD 기록
ord-4e661a1f3c4f4e15a3d6b823b6777323
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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