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

HRID 599212

Reaction equation

HRID 599212 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[S:23][C:22]([C:24](O)=[O:25])=[CH:21][CH:20]=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:22]3[S:23][C:19]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[CH:20][CH:21]=3)=[O:25])[CH2:3]1)[CH2:9]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 7364945-Phenyl-2-Thiophenecarboxylic AcidHCID 671521221-Azatricyclo[3.3.1.1,3,7]decan-4-amine hydrochloride

Product 1

HCID 671521075-Phenylthiophene-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-phenylthiophene-2-carboxylic acid (Maybridge) according to methods A and C; yield 62 mg, 0.17 mmol (53%): 1H NMR (300 MHz, methanol-d4) δ 2.08-2.27 (m, 5H), 2.47 (s, 2H), 3.48 (d, J=13 Hz, 2H), 3.55 (s, 2H), 3.81 (d, J=13 Hz, 2H), 4.25 (t, J=3 Hz, 1H), 7.32-7.47 (m, 4H), 7.65-7.71 (m, 2H), 7.83 (d, J=4 Hz, 1H); MS (DCI/NH3) m/z 339 (M+H)+; Anal. C20H22N2OS.HCl: C, H, N.

Sources & evidence

ORD record
ord-4816501204ef4f17857ec644e1477f12
Source dataset
uspto-grants-2011_03
Patent number
US07897766B2

Linked notes

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