{4-[4-(2-Aminoethyl)anilino]-1-piperidinyl}(3-methoxy-1-benzothiophen-2-yl)methanone → N-[3-[(2S)-2-Hydroxy-3-(2-[4-[1-(3-methoxy-benzo[b]thiophene-2-carbonyl)-piperidin-4-ylamino]-phenyl}-ethylamino)-propoxy}-phenyl]-acetamide

HRID 396076Notes

Reaction equation

HRID 396076 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:29]=[CH:28][C:7]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[S:18][C:19]4[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=4[C:21]=3[O:22][CH3:23])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[O:30]1[CH2:32][C@H:31]1[CH2:33][O:34][C:35]1[CH:36]=[C:37]([NH:41][C:42](=[O:44])[CH3:43])[CH:38]=[CH:39][CH:40]=1>>[OH:30][C@@H:31]([CH2:32][NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[S:18][C:19]4[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=4[C:21]=3[O:22][CH3:23])=[O:16])[CH2:13][CH2:14]2)=[CH:28][CH:29]=1)[CH2:33][O:34][C:35]1[CH:36]=[C:37]([NH:41][C:42](=[O:44])[CH3:43])[CH:38]=[CH:39][CH:40]=1

Participants

3

Reactant 2

HCID 18174005{4-[4-(2-Aminoethyl)anilino]-1-piperidinyl}(3-methoxy-1-benzothiophen-2-yl)methanoneHCID 23381346N-{3-[(2S)oxiranylmethoxy]phenyl}acetamide

Product 1

HCID 69985859N-[3-[(2S)-2-Hydroxy-3-(2-[4-[1-(3-methoxy-benzo[b]thiophene-2-carbonyl)-piperidin-4-ylamino]-phenyl}-ethylamino)-propoxy}-phenyl]-acetamideYield 23.4%

Procedure

{4-[4-(2-Aminoethyl)anilino]-1-piperidinyl}(3-methoxy-1-benzothiophen-2-yl)methanone (0.170 g, 0.415 mmol) was reacted with N-{3-[(2S)oxiranylmethoxy]phenyl}acetamide (0.086 g, 0.415 mmol) according to Procedure G to give the title compound (0.06 g, 0.097 mmol).

Sources & evidence

ORD record
ord-5f82b695ddd847039efedaf2799a3e78
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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