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

HRID 599211Notes

Reaction equation

HRID 599211 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.[C:13]1([C:19]2[CH:20]=[C:21]([C:24](O)=[O:25])[S:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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:24]([C:21]3[S:22][CH:23]=[C:19]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:20]=3)=[O:25])[CH2:3]1)[CH2:9]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 12231844-Phenylthiophene-2-carboxylic acidHCID 671521221-Azatricyclo[3.3.1.1,3,7]decan-4-amine hydrochloride

Product 1

HCID 671521434-Phenylthiophene-2-carboxylic acid (4r)-(1-azatricyclo[3.3.1.13,7]dec-4-yl)-amide hydrochloride

Procedure

Prepared from (4s)-1-azatricyclo[3.3.1.13,7]dec-4-ylamine hydrochloride and 4-phenylthiophene-2-carboxylic acid (Oakwood) according to methods A and C; yield 65 mg, 0.17 mmol (53%): 1H NMR (300 MHz, methanol-d4) δ 1.98 (d, J=14 Hz, 2H), 2.20 (s, 1H), 2.37 (d, J=14 Hz, 2H), 2.48 (s, 2H), 3.57 (s, 2H), 3.67 (d, J=1 Hz, 4H), 4.40 (s, 1H), 7.26-7.36 (m, 1H), 7.42 (t, J=7 Hz, 2H), 7.65-7.74 (m, 2H), 7.89 (d, J=1 Hz, 1H), 8.27 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 339 (M+H)+; Anal. C20H22N2OS.HCl 0.5H2O: C, H, N.

Sources & evidence

ORD record
ord-2b81c240230f42cc8170366050cc9a7a
Source dataset
uspto-grants-2011_03
Patent number
US07897766B2

Reaction notes

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