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

HRID 599217

Reaction equation

HRID 599217 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.[S:13]1[C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=[C:14]1[C:21]1[S:22][CH:23]=[CH:24][CH:25]=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:18]([C:17]3[S:13][C:14]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[CH:15][CH:16]=3)=[O:19])[CH2:3]1)[CH2:9]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1509652,2'-Bithiophene-5-carboxylic acidHCID 671521221-Azatricyclo[3.3.1.1,3,7]decan-4-amine hydrochloride

Product 1

HCID 671521142,2'-Bithiophene-5-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 2,2′-bithiophene-5-carboxylic acid (Acros) according to methods A and C; yield 105 mg, 0.27 mmol (76%): 1H NMR (300 MHz, methanol-d4) δ 1.97 (d, J=14 Hz, 2H), 2.20 (s, 1H), 2.32 (d, J=14 Hz, 2H), 2.47 (s, 2H), 3.56 (s, 2H), 3.66 (s, 4H), 4.37 (s, 1H), 7.08 (dd, J=5, 4 Hz, 1H), 7.24 (d, J=4 Hz, 1H), 7.35 (dd, J=4, 1 Hz, 1H), 7.43 (dd, J=5, 1 Hz, 1 H), 7.78 (d, J=4 Hz, 1H); MS (DCI/NH3) m/z 345 (M+H)+; Anal. C18H20N2OS2.HCl: C, H, N.

Sources & evidence

ORD record
ord-8dfd0521f51a41429bb81e5c1465c43c
Source dataset
uspto-grants-2011_03
Patent number
US07897766B2

Linked notes

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