(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazine → (1S)-N-(diphenylmethylene)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine

HRID 2056765Notes

Reaction equation

HRID 2056765 reaction equation
CS(O[CH2:6][CH2:7][C@H:8]1[C:13]2[CH:14]=[CH:15][C:16]([N:18]=[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:17][C:12]=2[CH2:11][CH2:10][O:9]1)(=O)=O.[F:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[C:39]([N:43]1[CH2:48][CH2:47][NH:46][C@H:45]([CH3:49])[CH2:44]1)=[CH:38][CH:37]=[CH:36]2>>[C:26]1([C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][C:16]2[CH:15]=[CH:14][C:13]3[C@H:8]([CH2:7][CH2:6][N:46]4[CH2:47][CH2:48][N:43]([C:39]5[C:40]6[C:35](=[CH:34][C:33]([F:32])=[CH:42][CH:41]=6)[CH:36]=[CH:37][CH:38]=5)[CH2:44][C@H:45]4[CH3:49])[O:9][CH2:10][CH2:11][C:12]=3[CH:17]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 69307275(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazineHCID 865960202-{(1S)-6-[(Diphenylmethylene)amino]-3,4-dihydro-1H-2-benzopyran-1-yl}ethyl methanesulfonate

Product 1

HCID 86596019(1S)-N-(diphenylmethylene)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine

Procedure

2-{(1S)-6-[(Diphenylmethylene)amino]-3,4-dihydro-1H-2-benzopyran-1-yl}ethyl methanesulfonate was coupled with (3R)-1-(6-fluoro-1-naphthyl)-3-methylpiperazine, as described for Example 1b), to yield (1S)-N-(diphenylmethylene)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine.

Sources & evidence

ORD record
ord-41a3c3f82f104817a4bb096d52e6b2b2
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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