2-Aminoadamantane hydrochloride → HCID 52952896, compound

HRID 1879492Notes

Reaction equation

HRID 1879492 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][N:9]([CH2:20][C:21]2[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=2)[CH2:24][N:25]2[CH:29]([C:30](O)=[O:31])[CH2:28][CH2:27][S:26]2(=[O:34])=[O:33])[C@H:10]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:6]([F:38])[C:5]([O:39][CH3:40])=[CH:4][CH:3]=1.Cl.[CH:42]12[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:50][CH:44]([CH2:45]3)[CH:43]1[NH2:52])[CH2:49]2>>[CH:42]12[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:50][CH:44]([CH2:45]3)[CH:43]1[NH:52][C:30]([CH:29]1[CH2:28][CH2:27][S:26](=[O:33])(=[O:34])[N:25]1[CH2:24][C:23]1[CH:35]=[CH:36][CH:37]=[C:21]([CH2:20][N:9]([CH2:8][C:7]3[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]([O:39][CH3:40])[C:6]=3[F:38])[C@H:10]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:11][C:12]([CH3:14])([CH3:15])[CH3:13])[CH:22]=1)=[O:31])[CH2:49]2

Participants

3

Reactant 2

HCID 253312-Aminoadamantane hydrochlorideHCID 58280450HCID 58280450, compound2×

Product 1

HCID 52952896HCID 52952896, compoundYield 66.2%

Procedure

2-(3-{[(6-Chloro-2-fluoro-3-methoxy-benzyl)-((S)-1 dimethylaminomethyl-3,3-dimethyl-butyl)-amino]-methyl}-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid (Intermediate 7, 0.093 g, 0.155 mmol) was reacted with 2-adamantanamine hydrochloride (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 0.036, 0.192 mmol) to form 2-(3-{[(6-Chloro-2-fluoro-3-methoxy-benzyl)-((S)-1-dimethylaminomethyl-3,3-dimethyl-butyl)-amino]-methyl}-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid adamantan-2-ylamide (0.075 g, 66%). m/z=731 (M+1); HRMS: calcd for C39H57ClFN4O4S. Calc [M+H+] 731.3768. found 731.3773.

Sources & evidence

ORD record
ord-cc92ec6103074d5fad000d7657140311
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

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