Ethyl Acetate → HCID 25028721, compound

HRID 1436382Notes

Reaction equation

HRID 1436382 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH:13][CH:14]([CH2:17][CH3:18])[CH2:15][OH:16])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[C:19](OCC)(=[O:21])C>CCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:13]3[CH:14]([CH2:17][CH3:18])[CH2:15][O:16][C:19]3=[O:21])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86618585HCID 86618585, compound

Product 1

HCID 25028721HCID 25028721, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In the same manner as described in step 4 of Example 1, replacing (2R)-2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}propan-1-ol with 2-[4-(4-bromo-phenyl)-thiazol-2-ylamino]-butan-1-ol, prepared in the previous step, and purification by flash chromatography using a solvent gradient of 10 to 20% ethyl acetate in hexane gave the title compound (155 mg, 72%) as a white solid; mp 148.5° C.; MS (ESI) m/z 353 [M+H]+. Anal. Calcd for C14H13BrN2O2S: C, 47.60; H, 3.71; N, 7.93. Found: C, 47.25; H, 3.64; N, 7.74. HRMS: calcd for C14H13BrN2O2S+H+, 352.99538; found (ESI, [M+H]+), 352.9939.

Workup

  1. customprepared in the previous step, and purification by flash chromatography

Sources & evidence

ORD record
ord-822e9107e58a49b18cfcc7b226275f5c
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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