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 1852196Notes

Reaction equation

HRID 1852196 reaction equation
[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]

Participants

4

Reactant 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

Product 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 hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-4e661a1f3c4f4e15a3d6b823b6777323
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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