Propylamine → HCID 10454896, compound

HRID 2293918Notes

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

Participants

Reactant 2

HCID 7852Propylamine

HCID 10340909HCID 10340909, compound

Product 1

HCID 10454896HCID 10454896, compoundYield 72.8%

Conditions

Temperature: 85 °C

Procedure

A mixture of compound 6 (22.5 mg, 0.056 mmol) and n-propylamine (2 mL) was stirred at 85° C. for 36 h. After evaporation of volatiles, the residue was purified by preparative TLC (chloroform-methanol, 20:1) to give compound 13 (17.3 mg, 72.8%) as a slightly yellow solid. 1H NMR (DMSO-d6) δ 0.85 (pseudo t, J=7.5 and 7.3 Hz, 3 H, CH3), 1.47 (sextet, J=7.2 Hz, 2 H, CH2), 3.30 (m, 2 H, CH2), 3.54 (s, 3 H, 9-CH3), 4.58 (br s, 2 H, CH2), 6.33 (br s, 1 H, exchangeable with D2O, NH), 7.10 (pseudo t, J=8.0 and 7.7 Hz, 1 H, H-16), 7.36 (d, J=7.7 Hz, 1 H, H-17), 7.57 (d, J=8.2 Hz, 1 H, H-15), 7.66 (s, 1 H, H-13), 7.72 (s, 1 H, H-8), 7.80 (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-1d96377a369e4520a98e6c1470c48573
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688774

Reaction notes

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