Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilane → [4-(3-Cyclopentyloxy-4-methoxy-phenyl)-piperidin-1-yl]-[4-(4-{2-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidin-1-yl]-methanone

HRID 395993Notes

Reaction equation

HRID 395993 reaction equation
C(O)=O.[NH2:4][CH2:5][CH2:6][C:7]1[CH:41]=[CH:40][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH:35]5[CH2:39][CH2:38][CH2:37][CH2:36]5)[CH:27]=4)[CH2:22][CH2:21]3)=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1.C([Si]([O:59][C:60]1[CH:65]=[CH:64][C:63]([O:66][CH2:67][CH:68]2[CH2:70][O:69]2)=[CH:62][CH:61]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>C(Cl)(Cl)Cl.CO>[CH:35]1([O:34][C:28]2[CH:27]=[C:26]([CH:23]3[CH2:22][CH2:21][N:20]([C:18]([N:15]4[CH2:14][CH2:13][CH:12]([NH:11][C:10]5[CH:40]=[CH:41][C:7]([CH2:6][CH2:5][NH:4][CH2:70][C@H:68]([OH:69])[CH2:67][O:66][C:63]6[CH:64]=[CH:65][C:60]([OH:59])=[CH:61][CH:62]=6)=[CH:8][CH:9]=5)[CH2:17][CH2:16]4)=[O:19])[CH2:25][CH2:24]3)[CH:31]=[CH:30][C:29]=2[O:32][CH3:33])[CH2:36][CH2:37][CH2:38][CH2:39]1

Participants

4

Reactant 2

HCID 12045564Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilaneHCID 69985596{4-[4-(2-Aminoethyl)anilino]-1-piperidinyl}{4-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-piperidinyl}methanone formate

Product 1

HCID 10233652[4-(3-Cyclopentyloxy-4-methoxy-phenyl)-piperidin-1-yl]-[4-(4-{2-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidin-1-yl]-methanoneYield 20.6%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

{4-[4-(2-Aminoethyl)anilino]-1-piperidinyl}{4-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-piperidinyl}methanone formate (0.50 g, 0.88 mmol) was reacted with tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenyl-silane (0.350 g, 0.88 mmol) according to Procedure G to yield (eluant: 20:1 chloroform-methanol) the title compound (0.168 g, 0.181 mmol)

Sources & evidence

ORD record
ord-8f9fa88bcbf3423b951809f00e352b6f
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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