Methanol → HCID 9819093, compound

HRID 2084040Notes

Reaction equation

HRID 2084040 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].CO.[CH3:11][NH:12][C@@H:13]1[CH2:22][C:21]2[C:16]3=[C:17]([NH:23][C:24](=[S:25])[N:15]3[CH2:14]1)[CH:18]=[CH:19][CH:20]=2>C(Cl)Cl>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:11][NH:12][C@@H:13]1[CH2:22][C:21]2[C:16]3=[C:17]([NH:23][C:24](=[S:25])[N:15]3[CH2:14]1)[CH:18]=[CH:19][CH:20]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 444266Maleic AcidHCID 9815850282522-93-4

Product 1

HCID 9819093HCID 9819093, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of maleic acid (0.317 g, 2.36 mmol) in a minimal amount of methanol (˜1 mL) is added to a mixture of (5R)-5-(methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione (VIII, EXAMPLE 7, 0.493 g, 2.25 mmol) in methylene chloride. The resulting solid is collected by filtration to give the title compound; mp=195-196°; [α]25D=−60° (c 0.93, methanol); IR (drift) 3140, 3112. 3060, 2969, 1627, 1619, 1568, 1481, 1455, 1398, 1389, 1361, 1220, 868 and 747 cm−1; NMR (300 MHz, CD3OD) δ 7.20-7.30, 7.10-7.20, 6.26, 4.49, 4.31, 4.05-4.20, 3.28 and 2.83; CMR (100 MHz, DMSO-d6+CD3OD) δ 170.4, 169.4, 136.6, 131.1, 130.9, 125.1, 122.1, 116.2, 109.6, 53.9, 43.1, 31.9 and 27.2; MS (ESI) m/z=220.1 (MH+).

Workup

  1. filtrationThe resulting solid is collected by filtration

Sources & evidence

ORD record
ord-e955462af3c94228b1b7f36fb5f153de
Source dataset
uspto-grants-2004_04
Patent number
US06716854B2

Reaction notes

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