Ethanol → HCID 86626619, compound

HRID 1747201Notes

Reaction equation

HRID 1747201 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13]([NH2:15])=[S:14])[CH:9]=[CH:10][CH:11]=1.Br.[C:17]([NH:20][C:21]1(NC2C=C(C=CC=2)C(O)=O)[NH:25][C:24]([CH3:31])(C2SC=NC=2)[CH2:23][S:22]1)(=[O:19])[CH3:18].[CH3:42][CH2:43]O>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13]2[S:14][CH:42]=[C:43]([C:23]3[S:22][C:21]([NH:20][C:17](=[O:19])[CH3:18])=[N:25][C:24]=3[CH3:31])[N:15]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 86626620HCID 86626620, compoundHCID 131731768HCID 131731768, compound2×

Product 1

HCID 86626619HCID 86626619, compound

Procedure

According to the general procedure 1, N-[3-(1,3-dioxolan-2-yl)phenyl]thiourea (prepared from 3-aminobenzyldehyde ethylene acetal (Alfa), following procedure D) is added to a solution of N-[5-(bromoacetyl)-4-methyl-1,3-thiazol-2-yl]acetamide (Intermediate 1) in EtOH. The mixture is stirred 5 hours at RT. The solvents are evaporated and the desired product is purified by crystallization. N-(2-{[3-(1,3-dioxolan-2-yl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)acetamide is isolated as a beige solid (320 mg; 88%). HPLC, Rt: 3.26 min (purity: 90.29%).

Workup

  1. customThe solvents are evaporated
  2. customthe desired product is purified by crystallization

Sources & evidence

ORD record
ord-833b66ec6da64caa80f283e1d201d7b6
Source dataset
uspto-grants-2015_10
Patent number
US09150561B2

Reaction notes

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