4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → 4-((2S)-2-Hydroxy-3-{1-[4-(toluene-4-sulfonyl)-phenyl]-piperidin-4-ylamino}-propoxy)-1,3-dihydro-benzoimidazol-2-one

HRID 1278769Notes

Reaction equation

HRID 1278769 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][C:4]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:24][CH2:25][C@H:26]([OH:39])[CH2:27][O:28][C:29]1[C:37]2[NH:36][C:35](=[O:38])[NH:34][C:33]=2[CH:32]=[CH:31][CH:30]=1>>[OH:39][C@@H:26]([CH2:25][NH:24][CH:19]1[CH2:20][CH2:21][N:16]([C:13]2[CH:12]=[CH:11][C:10]([S:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:23])=[CH:6][CH:5]=3)(=[O:9])=[O:8])=[CH:15][CH:14]=2)[CH2:17][CH2:18]1)[CH2:27][O:28][C:29]1[C:37]2[NH:36][C:35](=[O:38])[NH:34][C:33]=2[CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 227133581-[4-(Toluene-4-sulfonyl)-phenyl]-piperidin-4-one

Product 1

HCID 103022514-((2S)-2-Hydroxy-3-{1-[4-(toluene-4-sulfonyl)-phenyl]-piperidin-4-ylamino}-propoxy)-1,3-dihydro-benzoimidazol-2-one

Procedure

The title compound was prepared according to the procedure of Example 1 from 0.13 g (0.4 mmol) of Reference Example 25, 1-[4-(toluene-4-sulfonyl)-phenyl]-piperidin-4-one, and 0.13 g (0.6 mmol) of 4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydro-benzoimidazol-2-one, yielding 0.18 g of a white solid; m.p. 130-132° C.; MS (ES) m/z 537.0 (MH+); HRMS (FAB) Calcd. for C28H33N4O5S (MH+): 537.2166, Found: 537.2169.

Sources & evidence

ORD record
ord-6f488d7ceee844be943fa30956a410b0
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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