Ethanol, reaction products with ammonia, distn. residues → HCID 58932565, compound

HRID 853919Notes

Reaction equation

HRID 853919 reaction equation
O=[C:2]1[C:10]2([O:14][CH2:13][CH2:12][O:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:15]([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[CH2:23][O:24]OC)(=[O:17])=[O:16])[CH:8]=2)[N:3]1[CH2:27][C:28]1([CH2:35][NH2:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.N.[CH3:38]CO>>[CH3:38][O:24][CH2:23][C@@H:19]1[CH2:20][CH2:21][CH2:22][N:18]1[S:15]([C:7]1[CH:6]=[CH:5][C:4]2[N:3]3[CH2:27][C:28]4([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]4)[CH2:35][N:36]=[C:2]3[C:10]3([O:14][CH2:13][CH2:12][O:11]3)[C:9]=2[CH:8]=1)(=[O:16])=[O:17]

Participants

3

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 86601548HCID 86601548, compound

Product 1

HCID 58932565HCID 58932565, compoundYield 58%

Procedure

A solution of 1-{[2′-oxo-5′-{[(2S)-2-(methoxyoxymethyl)pyrrolidin-1-yl]sulfonyl}spiro[1,3-dioxolane-2,3′-indol]-1′(2′H)-yl]methyl}-1-(aminomethyl)-cycloheptane (0.25 g, 0.49 mmol, 1 eq) in 2N ammonia/EtOH (5 mL) was heated in a sealed tube at 130° C. for 4 hours. After cooling, the mixture was concentrated and the residue was purified by chromatography on Biotage KP silica gel eluting with hexane/acetone (3:1) to give the title compound as an off-white solid (0.14 g, 58% yield). NMR (500 MHz, DMSO-d6): consistent. MS (API-ES+) m/z 490 [M+H].

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. customthe residue was purified by chromatography on Biotage KP silica gel eluting with hexane/acetone (3:1)

Sources & evidence

ORD record
ord-0a31ccb4595c4fbe9a18726988861c2c
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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