HCID 178478697, compound → HCID 178478926, compound

HRID 1422450Notes

Reaction equation

HRID 1422450 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[NH:5][C:6](=[CH:10][CH2:11][CH2:12][NH2:13])[C:7](=[O:9])[N:8]=1.Cl.NC1NC=C(CCCN[C:25]([C:27]2[N:28]([CH3:34])[C:29]([Br:33])=[C:30]([Br:32])[CH:31]=2)=[O:26])N=1>>[ClH:1].[NH2:3][C:4]1[NH:5][C:6](=[CH:10][CH2:11][CH2:12][NH:13][C:25]([C:27]2[N:28]([CH3:34])[C:29]([Br:33])=[C:30]([Br:32])[CH:31]=2)=[O:26])[C:7](=[O:9])[N:8]=1

Participants

3

Reactant 2

HCID 178478697HCID 178478697, compoundHCID 178478925HCID 178478925, compound

Product 1

HCID 178478926HCID 178478926, compoundYield 47%

Procedure

Using the same general procedure as used for 2-amino-5-(3-amino-propylidene)-1,5-dihydro-imidazol-4-one dihydrochloride, 0.100 g of dihydrosventrin hydrochloride 23 gave 0.048 g (47%) of the title compound 32 as a tan solid ((Z)-isomer exclusively). 1H NMR (300 MHz, CD3OD) δ 6.84 (s, 1H), 6.16 (t, 1H, J=7.8 Hz), 3.91 (s, 3H), 3.46 (t, 2H, J=6.9 Hz), 2.59 (dt, 2H, J=6.9, 14.7 Hz); 13C NMR (100 MHz, DMSO-d6) δ 163.80, 163.00, 157.19, 130.63, 129.04, 119.42, 115.92, 112.67, 99.09, 39.06, 36.28, 28.73; HRMS (ESI) calcd for C12H14Br2N5O2 (MH+) 417.9509, found 417.9511.

Sources & evidence

ORD record
ord-0d16de46efc94dcdb897229b10391d8d
Source dataset
uspto-grants-2015_01
Patent number
US08927029B2

Reaction notes

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