1,4-Dioxane hydrochloride → Cyclopropanesulfonic acid [14-amino-18-(isoquinolin-1-yloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carbonyl)-amide bis hydrochloride

HRID 346941Notes

Reaction equation

HRID 346941 reaction equation
C(OC(=O)[NH:7][CH:8]1[C:26](=[O:27])[N:25]2[CH:21]([CH2:22][CH:23]([O:28][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][N:30]=3)[CH2:24]2)[C:20](=[O:39])[NH:19][C:18]2([C:40]([NH:42][S:43]([CH:46]3[CH2:48][CH2:47]3)(=[O:45])=[O:44])=[O:41])[CH:16]([CH2:17]2)[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)(C)(C)C.[ClH:50].O1CCOCC1>>[ClH:50].[ClH:50].[NH2:7][CH:8]1[C:26](=[O:27])[N:25]2[CH:21]([CH2:22][CH:23]([O:28][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][N:30]=3)[CH2:24]2)[C:20](=[O:39])[NH:19][C:18]2([C:40]([NH:42][S:43]([CH:46]3[CH2:47][CH2:48]3)(=[O:44])=[O:45])=[O:41])[CH:16]([CH2:17]2)[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 72804543HCID 72804543, compound

Product 1

HCID 86597622Cyclopropanesulfonic acid [14-amino-18-(isoquinolin-1-yloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carbonyl)-amide bis hydrochlorideYield 92%

Procedure

A stirred slurry of [4-cyclopropane-sulfonylaminocarbonyl-18-(isoquinolin-1-yloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester (1.20 g, 1.7 mmol) was treated with 4N HCl/dioxane (Aldrich)(10 mL) for 4 h. The reaction mixture was concentrated in vacuo to give 1.10 g (92%) of cyclopropanesulfonic acid [14-amino-18-(isoquinolin-1-yloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carbonyl]-amide bis hydrochloride as a white solid: LC-MS (Method B, retention time: 1.39 min), MS m/z 596 (M++1–2HCl).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-eb879f3b5a644d8898a53161f442e6f0
Source dataset
uspto-grants-2007_02
Patent number
US07173004B2

Reaction notes

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