Hydrochloric Acid → N1-(2-aminophenyl)-N7-(pyridin-3-ylmethyl)heptanediamide

HRID 2276698Notes

Reaction equation

[O:1]=[C:2]([NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17]C(=O)OC(C)(C)C)=[O:9].Cl>CCOC(C)=O>[NH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:1]

Participants

Conditions

Temperature: 0 °C

Procedure

Into a solution of tert-butyl (2-(7-oxo-7-((pyridin-3-ylmethyl)amino)heptanamido)phenyl)carbamate (1.2 g, 2.73 mmol) in EtOAc (50 mL) were passed HCl (gas) at 0° C. The mixture was stirred for 30 min at 0° C. under HCl (gas). A white solid precipitated and was filtered. The white solid was collected and poured into a solution of 5% Na2CO3 in water (100 mL). The resulting mixture was extracted by EtOAc (100 mL×2). The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduce pressure. The crude solid was recrystallized in EtOAc to afford the desired compound (0.6 g, yield 64.6%) as an off-white solid.

Workup

customat 0° C
customA white solid precipitated
filtrationwas filtered
customThe white solid was collected
additionpoured into a solution of 5% Na2CO3 in water (100 mL)
extractionThe resulting mixture was extracted by EtOAc (100 mL×2)
dry with materialdried with anhydrous Na2SO4
concentrationconcentrated
customThe crude solid was recrystallized in EtOAc

Sources & evidence

ORD record: ord-753fac27aac94eb2b79eb9cbb9968542
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133105B2

Reaction notes

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