Diisopropylethylamine → [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 tetrahydro-pyran-4-yl ester

HRID 346944Notes

Reaction equation

HRID 346944 reaction equation
Cl.Cl.[NH2:3][CH:4]1[C:22](=[O:23])[N:21]2[CH:17]([CH2:18][CH:19]([O:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][N:26]=3)[CH2:20]2)[C:16](=[O:35])[NH:15][C:14]2([C:36]([NH:38][S:39]([CH:42]3[CH2:44][CH2:43]3)(=[O:41])=[O:40])=[O:37])[CH:12]([CH2:13]2)[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.CCN(C(C)C)C(C)C.Cl[C:55]([OH:57])=[O:56].[O:58]1[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59]1>C(Cl)Cl>[O:58]1[CH2:63][CH2:62][CH:61]([O:57][C:55](=[O:56])[NH:3][CH:4]2[C:22](=[O:23])[N:21]3[CH:17]([CH2:18][CH:19]([O:24][C:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH:28]=[CH:27][N:26]=4)[CH2:20]3)[C:16](=[O:35])[NH:15][C:14]3([C:36]([NH:38][S:39]([CH:42]4[CH2:43][CH2:44]4)(=[O:40])=[O:41])=[O:37])[CH:12]([CH2:13]3)[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:60][CH2:59]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 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 hydrochlorideHCID 86597623Tetrahydropyran chloroformate

Product 1

HCID 72427458[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 tetrahydro-pyran-4-yl esterYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from 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 (50 mg, 0.075 mmol, 44 μL (0.25 mmol) of DIPEA and 0.17 mL (0.1 mmol) of tetrahydropyran chloroformate (prepared by treating tetrahydro-pyran-4-ol with phosgene) in DCM as described in the procedure above to give 28 mg (52%) of a white solid. Preparative HPLC condition: YMC XTERRA, S5, 19×100 mm, gradient: 50% B to 100% B, 10 min, hold 2 min, flow rate 25 mL/min. LC-MS (Method A, retention time: 3.13 min), MS m/z 724 (M++1).

Sources & evidence

ORD record
ord-8d61e7322e4a4418bc52a5c45e5551db
Source dataset
uspto-grants-2007_02
Patent number
US07173004B2

Reaction notes

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