HCID 67087005, compound → HCID 178508784, compound

HRID 1665091Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:13][NH2:14])[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[NH2:15][C:16]1[C:17]([C:24]([NH:26][C:27](=N)SC)=[O:25])=[N:18][C:19]([Cl:23])=[C:20]([NH2:22])[N:21]=1>CC(O)C>[OH:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][CH2:3][C@@H:2]2[CH2:13][NH:14]/[C:27](=[N:26]\[C:24]([C:17]3[C:16]([NH2:15])=[N:21][C:20]([NH2:22])=[C:19]([Cl:23])[N:18]=3)=[O:25])/[NH:1]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a stirred solution of (4-((R)-4,5-Diamino-pentyl)-phenol (intermediate K) (1.5 g, 7.72 mmol) in propan-2-ol (100 ml) at 30° C. is added in one portion 1-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea (Intermediate A) and the reaction is heated at 30° C. for 18 hours followed by 50° C. for a further 18 hours. The reaction mixture is filtered hot and the filtrate solvent is removed in vacuo to afford a yellow foam. The foam is purified by chromatography (SiO2, DCM/MeOH/5% NH3) to afford the title compound; [M+H]+ 390

Workup

filtrationThe reaction mixture is filtered hot
customthe filtrate solvent is removed in vacuo
customto afford a yellow foam
customThe foam is purified by chromatography (SiO2, DCM/MeOH/5% NH3)

Sources & evidence

ORD record: ord-d08afdfc01cf473f991f8b863171f9bd
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039472B2

Reaction notes

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