N,N-Dimethylsulfamide → HCID 68929729, compound

HRID 1453361Notes

Reaction equation

HRID 1453361 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16](O)=[O:17])=[CH:13][CH:14]=3)[CH:9]([CH2:19][CH2:20][C:21](=[O:34])[N:22]3[CH2:27][CH2:26][CH:25]([N:28]4[CH2:32][CH2:31][CH2:30][C:29]4=[O:33])[CH2:24][CH2:23]3)[C:8]=2[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:41][N:42]([CH3:47])[S:43]([NH2:46])(=[O:45])=[O:44].Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.CC(N(C)C)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([NH:46][S:43]([N:42]([CH3:47])[CH3:41])(=[O:45])=[O:44])=[O:17])=[CH:13][CH:14]=3)[CH:9]([CH2:19][CH2:20][C:21](=[O:34])[N:22]3[CH2:23][CH2:24][CH:25]([N:28]4[CH2:32][CH2:31][CH2:30][C:29]4=[O:33])[CH2:26][CH2:27]3)[C:8]=2[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 134472N,N-DimethylsulfamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68846810HCID 68846810, compound

Product 1

HCID 68929729HCID 68929729, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 1-cyclohexyl-3-(3-oxo-3-(4-(2-oxopyrrolidin-1-yl)piperidin-1-yl)propyl)-2-phenyl-3H-indene-5-carboxylic acid, (46 mg, 0.083 mmol), N,N-dimethylsulfamide (51 mg, 0.42 mmol) and DMAP (51 mg, 0.42 mmol) in dimethylacetamide (1 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (64 mg, 0.33 mmol). The reaction solution was stirred in a sealed tube under nitrogen at 50° C. overnight and purified by reverse phase prep-HPLC to yield 1-cyclohexyl-N-[(dimethylamino)sulfonyl]3-(3-oxo-3-(4-(2-oxopyrrolidin-1-yl)piperidin-1-yl)propyl)-2-phenyl-3H-indene-5-carboxamide as an off-white solid. 1H NMR (500 MHz, CDCl3) δ 8.91 (br s, 1H), 8.09 (s, 1H), 7.92 (d, J=8.5 Hz, 1H), 7.57-7.41 (m, 5H), 6.86 (s, 1H), 5.10 (br s, 1H), 4.41 (br s, 1H), 4.05-3.50 (m, 7H), 3.07 (s, 6H), 2.81 (m, 1H), 2.44 (m, 2H), 2.05-1.38 (m, 16H). LCMS: m/e 658 (M+H)+, ret time 2.43 min, column 3, 2 minute gradient. The next set of experimental procedures constitute a the start of a new section which stand alone:

Workup

  1. custompurified by reverse phase prep-HPLC

Sources & evidence

ORD record
ord-91ae0284c9034252ac6ff5936aaaf689
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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