Ammonia → 5-(3-Trifluoromethylphenyl)-furan-2-carboxylic acid(4r)-(1-azatricyclo[3.3.1.13,7]dec-4-yl)-amide hydrochloride

HRID 599218

Reaction equation

HRID 599218 reaction equation
[ClH:1].[N:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C@H:5]3[NH2:12])[CH2:3]1)[CH2:9]2.[F:13][C:14]([F:30])([F:29])[C:15]1[CH:16]=[C:17]([C:21]2[O:25][C:24]([C:26](O)=[O:27])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1.N>>[ClH:1].[N:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C@H:5]3[NH:12][C:26]([C:24]3[O:25][C:21]([C:17]4[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:30])([F:13])[F:29])[CH:16]=4)=[CH:22][CH:23]=3)=[O:27])[CH2:3]1)[CH2:9]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6882815-(3-(Trifluoromethyl)phenyl)-2-furoic acidHCID 671521221-Azatricyclo[3.3.1.1,3,7]decan-4-amine hydrochloride

Product 1

HCID 671521055-(3-Trifluoromethylphenyl)-furan-2-carboxylic acid(4r)-(1-azatricyclo[3.3.1.13,7]dec-4-yl)-amide hydrochloride

Procedure

Prepared from (4r)-1-azatricyclo[3.3.1.13,7]dec-4-ylamine hydrochloride and 5-[3-(trifluoromethyl)phenyl]-2-furoic acid (Aldrich) according to methods A and C; yield 29 mg, 0.07 mmol (31%): 1H NMR (300 MHz, methanol-d4) δ 2.09-2.30 (m, 5H), 2.52 (s, 2H), 3.50 (d, J=13 Hz, 2H), 3.57 (s, 2H), 3.83 (d, J=13 Hz, 2H), 4.28 (s, 1H), 7.12 (d, J=4 Hz, 1H), 7.34 (d, J=4 Hz, 1H), 7.63-7.69 (m, 2H), 8.10-8.18 (m, 1H), 8.24 (s, 1H); MS (DCI/NH3) m/z 391 (M+H)+; Anal. C21H21F3N2O2.HCl 0.9H2O: C, H, N.

Sources & evidence

ORD record
ord-db83d79143474a1ba7432bcd40e80ac0
Source dataset
uspto-grants-2011_03
Patent number
US07897766B2

Linked notes

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