Pyridinium chloride → HCID 131719658, compound

HRID 1900904Notes

Reaction equation

C(O)(=O)C.[C:5]([C:8]1[CH:32]=[CH:31][C:11]([C:12]([NH:14][C:15](=[O:30])[NH:16][C:17]2[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=2)=[O:13])=[CH:10][CH:9]=1)(=[NH:7])[NH2:6].[ClH:33].N1C=CC=CC=1>CO>[ClH:33].[C:5]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][C:15](=[O:30])[NH:16][C:17]2[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=2)=[O:13])=[CH:31][CH:32]=1)(=[NH:6])[NH2:7]

Participants

Conditions

Temperature: 10 °C

Procedure

To a suspension of ethyl 4-[3-(4-amidinobenzoyl)ureido]phenoxyacetate, acetate salt (1.3 g), in methanol (60 ml) was added a solution of pyridine hydrochloride (400 mg) in methanol (5 ml). The resultant mixture was sonicated for 5 minutes and then heated to boiling. The resultant solution was filtered hot and diluted to turbidity with ether. On cooling to 10° C., a solid precipitated which was collected, washed with ether and recrystallised from methanol/ether to give the title compound (500 mg) as an off-white crystalline solid: m.p. 246°-250° C. (decomposes); NMR Spectrum (DMSO-d6) 1.23 (3H, t), 4.18 (2H, q), 4.76 (2H, s), 6.95 (2H, d), 7.50 (2H, d), 7.96 (2H, d), 8.20 (2H, d), 9.28 (2H, br s), 9.53 (2H, br s), 10.58 (1H, s), 11.22 (1H, s); Mass Spectrum m/Z 385 (M+H)+ ; Elemental Analysis: calculated for C19H20N4O5. 1.0 HCl: C, 54.2%; H, 5.03%; N, 13.3%; found: C, 54.4%; H, 4.9%; N, 13.3%.

Workup

temperatureheated to boiling
filtrationThe resultant solution was filtered hot
additiondiluted to turbidity with ether
customa solid precipitated which
customwas collected
washwashed with ether
customrecrystallised from methanol/ether

Sources & evidence

ORD record: ord-d6bef1f791fb41d0ba6198913f8c9225
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576334

Reaction notes

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