((S)-4,5-Diamino-pentyl)-carbamic acid benzyl ester → HCID 178508794, compound

HRID 2281572Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13](=[NH:16])SC)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[CH2:17]([O:24][C:25](=[O:34])[NH:26][CH2:27][CH2:28][CH2:29][C@H:30]([NH2:33])[CH2:31]N)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(O)C>[CH2:17]([O:24][C:25](=[O:34])[NH:26][CH2:27][CH2:28][CH2:29][C@H:30]1[CH2:31][NH:16]/[C:13](=[N:12]\[C:10]([C:3]2[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=2)=[O:11])/[NH:33]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 85 °C

Procedure

1-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea (Intermediate A) (0.97 g, 3.72 mmol) is stirred in a three necked round bottom flask fitted with a bleach trap and condenser and ((S)-4,5-Diamino-pentyl)-carbamic acid benzyl ester (Intermediate S) (0.85 g, 3.38 mmol) in propan-2-ol (20 ml) is added. The reaction mixture is stirred at 85° C. for 66 hours. Purification by catch and release resin (SCX-2) followed by elution through a silica pad flushed with EtOAc, ethanol and MeOH yields the title compound as an orange foam; [M+H]+ 447.1

Workup

customfitted with a bleach trap and condenser
customPurification by catch and release resin (SCX-2)
washfollowed by elution through a silica pad
customflushed with EtOAc, ethanol and MeOH

Sources & evidence

ORD record: ord-c7416e0d9e5649b1b4d45bda5689bf2b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139586B2

Reaction notes

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