Hexylamine → HCID 10457142, compound

HRID 2293919Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[N:3]=1.[CH2:21]([NH2:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>>[CH2:21]([NH:27][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[N:3]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

Reactant 2

HCID 8102Hexylamine

HCID 10340909HCID 10340909, compound

Product 1

HCID 10457142HCID 10457142, compoundYield 86%

Conditions

Temperature: 80 °C

Procedure

A mixture of compound 6 (23.5 mg, 0.059 mmol) and n-hexylamine (1 mL) was heated for 4.5 days at 80° C. After evaporation of volatiles, the residue was purified by preparative TLC (chloroform-methanol, 20:1) to give compound 14 (23.5 mg, 86.0%). 1H NMR (DMSO-d6) δ 0.84 (m, 3 H, CH3), 1.25 (m, 6 H, CH2), 1.45 (m, 2 H, CH2), 3.17 (m, 2 H, CH2), 3.54 (s, 3 H, 9-CH3), 4.58 (br s, 2 H, CH2), 6.32 (br s, 1 H, exchangeable with D2O, NH), 7.09 (pseudo t, J=7.8 and 7.6 Hz, 1 H, H-16), 7.35 (d, J=7.8 Hz, 1 H, H-17), 7.57 (d, J=7.7 Hz, 1 H, H-15), 7.66 (s, 1 H, H-13), 7.71 (s, 1 H, H-8), 7.82 (br s, 1 H, exchangeable with D2O, NH).

Workup

customAfter evaporation of volatiles
customthe residue was purified by preparative TLC (chloroform-methanol, 20:1)

Sources & evidence

ORD record: ord-6959b22938b0452db0d6311fd7933d60
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688774

Reaction notes

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