Isobutylamine → HCID 90310832, compound

HRID 1519165Notes

Reaction equation

[CH:1]1([C:5]2[CH:10]=[CH:9][C:8]([C:11]3[N:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=3)=[C:7]([F:18])[C:6]=2[O:19][CH2:20][CH:21]2[CH2:23][O:22]2)[CH2:4][CH2:3][CH2:2]1.[CH2:24]([NH2:28])[CH:25]([CH3:27])[CH3:26]>CO>[NH2:17][C:14]1[N:15]=[CH:16][C:11]([C:8]2[C:7]([F:18])=[C:6]([C:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)=[CH:10][CH:9]=2)[O:19][CH2:20][CH:21]([OH:22])[CH2:23][NH:28][CH2:24][CH:25]([CH3:27])[CH3:26])=[N:12][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-(4-cyclobutyl-2-fluoro-3-(oxiran-2-ylmethoxy)phenyl)pyrazin-2-amine (150 mg, 0.48 mmol), isobutylamine (105 mg, 1.43 mmol) and MeOH (5 mL) was heated in sealed tube to 60° Celsius for 5 hours, then the solvent was removed. The residue was subjected to FCC to give the titled compound (125 mg, 67%). MS (CI): mass calcd. for C21H29FN4O2, 388.23; m/z found, 389.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.48-8.39 (m, 1H), 8.08 (d, J=1.4, 1H), 7.54 (m, 1H), 7.14 (d, J=8.2, 1H), 4.72 (s, 2H), 4.45-4.37 (m, 1H), 4.09-3.99 (m, 2H), 3.86-3.73 (m, 1H), 3.29-3.21 (m, 1H), 3.16-3.07 (m, 1H), 2.86-2.69 (m, 2H), 2.41-2.30 (m, 2H), 2.19-2.01 (m, 4H), 1.90-1.81 (m, 1H), 1.05 (d, J=6.7, 6H).

Workup

customthe solvent was removed

Sources & evidence

ORD record: ord-7b6078e68e754b74b502dd4ff8d8101b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073876B2

Reaction notes

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