3-(2-Methyl-1,3-thiazol-4-yl)benzaldehyde → 6-(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)-1-(3-(2-methylthiazol-4-yl)benzyl)piperidin-2-one

HRID 594653Notes

Reaction equation

HRID 594653 reaction equation
[NH2:1][CH:2]([C:10]1[C:19]2[O:18][CH2:17][CH2:16][O:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8]C)=O.[CH3:20][C:21]1[S:22][CH:23]=[C:24]([C:26]2[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=2)[CH:29]=O)[N:25]=1>>[O:15]1[CH2:16][CH2:17][O:18][C:19]2[C:10]([CH:2]3[N:1]([CH2:29][C:28]4[CH:31]=[CH:32][CH:33]=[C:26]([C:24]5[N:25]=[C:21]([CH3:20])[S:22][CH:23]=5)[CH:27]=4)[C:6](=[O:8])[CH2:5][CH2:4][CH2:3]3)=[CH:11][CH:12]=[CH:13][C:14]1=2

Participants

3

Reactant 2

HCID 71277823-(2-Methyl-1,3-thiazol-4-yl)benzaldehydeHCID 69095861Methyl 5-amino-5-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)pentanoate

Product 1

HCID 690809836-(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)-1-(3-(2-methylthiazol-4-yl)benzyl)piperidin-2-one

Procedure

Prepared according to the described general procedure 1 (GP1) by reaction of methyl 5-amino-5-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)pentanoate with commercially available 3-(2-methylthiazol-4-yl)benzaldehyde. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.81 min.; [M+H]+: 420.98 g/mol.

Workup

  1. customPrepared
  2. customSubsequent purification by preparative HPLC
  3. customafforded the target compound

Sources & evidence

ORD record
ord-a75dfea83ea0418b93cd26370f7a5c66
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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