Diisopropylethylamine → HCID 118036981, compound

HRID 1777915Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[C:8](F)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.Cl.[NH2:12][C@@H:13]1[C@@H:18]2[CH2:19][C@@H:15]([CH2:16][CH2:17]2)[C@@H:14]1[CH2:20][OH:21].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CCOC(C)=O>[NH2:1][C:2]1[CH:9]=[C:8]([NH:12][C@H:13]2[C@@H:14]([CH2:20][OH:21])[C@H:15]3[CH2:19][C@@H:18]2[CH2:17][CH2:16]3)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 6-amino-4-fluoronicotinonitrile (intermediate 21, 280 mg, 2.04 mmol) and racemic ((1R*,2S*,3R*,4S*)-3-aminobicyclo[2.2.1]heptan-2-yl)methanol hydrochloride (435 mg, 2.45 mmol) in NMP (5 ml) was treated with DIPEA (1.07 ml, 6.13 mmol), stirred at 100° C. for 6 h and at 180° C. (MW) for 30 min. The reaction mixture was diluted in EtOAc and washed with water (2×) and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by normal phase chromatography (24 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a beige solid. (UPLC-MS 3) tR 0.53 min; ESI-MS 259.2 [M+H]+.

Workup

washwashed with water (2×) and brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by normal phase chromatography (24 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100)

Sources & evidence

ORD record: ord-8e1977fd30e54f5da05e83b66a7a6332
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266883B2

Reaction notes

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