Pyridine → HCID 71115087, compound

HRID 1502355Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1.[CH2:20]([N:22]=[C:23]=[O:24])[CH3:21].N1C=CC=CC=1>ClCCl>[CH2:20]([NH:22][C:23]([NH:18][C:13]1[N:14]=[CH:15][C:16]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[CH3:19])[CH:17]=2)=[O:24])[CH3:21]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 7-(5-fluoro-2-methylphenyl)isoquinolin-3-amine (51.3 mg, 203 μmol) and ethyl isocyanate (20 uL, 0.26 mmol) in dichloromethane (2.0 mL) was heated at 40° C. for 4 days. The cooled mixture was treated with pyridine (20 uL, 0.25 mmol) and a further portion of ethyl isocyanate (20 uL, 0.26 mmol) at 40° C. for 24 h and concentrated in vacuo, and the residue purified by reverse phase HPLC (gradient of acetonitrile in water with 0.1% formic acid) to yield the title compound as a white amorphous solid (54.6 mg, 83%). 1H NMR (400 MHz, DMSO) δ 9.07 (s, 2H), 8.09 (s, 1H), 7.97 (s, 1H), 7.84 (d, J=8.5 Hz, 1H), 7.65 (d, J=8.4 Hz, 1H), 7.37 (t, J=7.2 Hz, 1H), 7.20-7.12 (m, 2H), 7.06-7.00 (s, 1H), 3.19 (dq, J=7, 7 Hz, 2H), 2.25 (s, 3H), 1.10 (t, J=7.2 Hz, 3H). LCMS (Method E): RT=4.885 min, M+H+=324.1.

Workup

concentrationconcentrated in vacuo
customthe residue purified by reverse phase HPLC (gradient of acetonitrile in water with 0.1% formic acid)

Sources & evidence

ORD record: ord-51aa61e02667472fb87d65ade5f2575a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206175B2

Reaction notes

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