Cyclopropanesulfonamide → HCID 72804543, compound

HRID 346934Notes

Reaction equation

HRID 346934 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:27](=[O:28])[N:26]2[CH:22]([CH2:23][CH:24]([O:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][N:31]=3)[CH2:25]2)[C:21](=[O:40])[NH:20][C:19]2([C:41](O)=[O:42])[CH:17]([CH2:18]2)[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:44]1([S:47]([NH2:50])(=[O:49])=[O:48])[CH2:46][CH2:45]1>CO.C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[C:27](=[O:28])[N:26]2[CH:22]([CH2:23][CH:24]([O:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][N:31]=3)[CH2:25]2)[C:21](=[O:40])[NH:20][C:19]2([C:41]([NH:50][S:47]([CH:44]3[CH2:46][CH2:45]3)(=[O:49])=[O:48])=[O:42])[CH:17]([CH2:18]2)[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 15765418CyclopropanesulfonamideHCID 7242743414-Tert-butoxycarbonylamino-18-(isoquinolin-1-yloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]-nonadec-7-ene-4-carboxylic acid

Product 1

HCID 72804543HCID 72804543, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared from 14-tert-butoxycarbonylamino-18-(isoquinolin-1-yloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]-nonadec-7-ene-4-carboxylic acid etherate (100 mg, 0.15 mmol) and cyclopropylsulfonamide (24 mg, 0.20 mmol) as described in the general procedure above. Flash chromatography (2% methanol/methylene chloride) gave 55 mg (53%) of [4-cyclopropanesulfonylaminocarbonyl-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 as a white powder: 1H NMR (500 MHz, CD3Cl3) δ 0.89–0.95 (m, 1H), 1.03–1.16 (m, 3H), 1.22 (s, 9H), 1.18–1.48 (m, 8H), 1.78 (m, 1H), 1.87 (m, 1H), 1.94 (m, 1H), 2.29 (q, J=9.0 Hz, 1H), 2.56 (m, 1H), 2.67 (dd, J=7.9 Hz, 2.7 Hz, 2H), 2.90 (m, 1H), 4.04 (dd, J=11.3 Hz, 4.0 Hz, 1H), 4.29 (m, 1H), 4.61 (m, 2H), 4.97–5.03 (m, 2H), 5.70 (m, 1H), 5.94 (s, 1H), 6.67 (s, 1H), 7.25 (m, 1H), 7.47 (t, J=7.3 Hz, 1H), 7.64 (t, J=7.3 Hz, 1H), 7.72 (d, J=7.9 Hz, 1H), 7.97 (d, J=5.8 Hz, 1H), 8.17 (d, J=8.5 Hz, 1H), 10.20 (s, 1H). LC-MS (Method A, retention time: 3.67 min), MS m/z 696 (M++1).

Sources & evidence

ORD record
ord-e7eea0855e8f4208981b168c6a1c3b1a
Source dataset
uspto-grants-2007_02
Patent number
US07173004B2

Reaction notes

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