Acetic Acid → HCID 44218572, compound

HRID 1928806Notes

Reaction equation

[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(O)(=O)C.[C:26]([O:30][C:31](=[O:37])[N:32]([CH3:36])[CH2:33][CH:34]=O)([CH3:29])([CH3:28])[CH3:27].C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO>[C:26]([O:30][C:31](=[O:37])[N:32]([CH2:33][CH2:34][NH:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:10][C@H:1]1[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]1)[CH:20]=[CH:19]2)[CH3:36])([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of (R)—N2-indan-1-yl-quinoline-2,6-diamine (453 mg, 1.645 mmol) in Methanol (10 mL) with acetic acid (0.3 mL, 4.935 mmol) and commercially available methyl-(2-oxo-ethyl)carbamic acid tert-butyl ester (300 mg, 1.731 mmol) was stirred at 23° C. for 1 h. Portionwise addition of sodium cyanoborohydride (286 mg, 4.11 mmol) was followed by additional stirring at 23° C. for 3 h. Poured onto saturated NaHCO3-solution and extracted twice with ethyl acetate, dried over Na2SO4 and evaporated totally gave a crude product which was purified by flash chromatography with heptane and ethyl acetate to give the title compound as a yellow foam (550 mg, 73%); MS: m/e=433.4 (M+H+).

Workup

stirringby additional stirring at 23° C. for 3 h
extractionextracted twice with ethyl acetate
dry with materialdried over Na2SO4
customevaporated totally
customgave a crude product which
customwas purified by flash chromatography with heptane and ethyl acetate

Sources & evidence

ORD record: ord-104bd243103540f4a60a03e7b419e161
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183380B2

Reaction notes

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