Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → HCID 58295714, compound

HRID 390157

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:29]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15](=[O:28])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:11][CH2:10]1)[CH2:8][CH:7]2[NH:30]C(=O)OCC[Si](C)(C)C.[N+](CC)(CC)(CC)CC.[F-]>CC#N>[NH2:30][CH:7]1[C:6]2[C:29](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=2)[C:9]2([CH2:14][CH2:13][N:12]([C:15](=[O:28])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:25])([F:26])[F:27])[CH2:11][CH2:10]2)[CH2:8]1

Participants

Conditions

Temperature: 100 °C

Procedure

(±)-(E)-2-(trimethylsilyl)ethyl 7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-ylcarbamate (16.5 mg, 0.026 mmol) and Et4NF (30 mg) were dissolved in MeCN (3 mL). The solution was heated at 100° C. for 10 min in a microwave. The solution was concentrated and the residue was purified by preparative HPLC to give (±)-(E)-1-(3-amino-7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-yl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one (11 mg, 70%) as its TFA salt. LC-MS Method 1 tR=1.38, min, m/z=479, 481; 1H NMR (CD3OD) 1.53 (m, 1H), 1.67 (m, 1H), 2.08 (m, 1H), 2.55 (m, 1H), 2.9-3.5 (5H), 4.38 (d, 1H), 4.72 (d, 1H), 7.2-8.0 (9H).

Workup

concentrationThe solution was concentrated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-f91e544cfc5d460e8abc75187bb983f4
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383629B2

Linked notes

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