HCID 1479743, compound → HCID 68406993, compound

HRID 888042Notes

Reaction equation

HRID 888042 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:33]1([NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]2[S:47][C:46](Cl)=[N:45][CH:44]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>C(OCC)(=O)C>[CH:33]1([NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]2[S:47][C:46]([C:20]3[CH:19]=[CH:18][C:17]([C:16]([NH:15][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:32])=[CH:22][CH:21]=3)=[N:45][CH:44]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 1479743HCID 1479743, compoundHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 1

HCID 68406993HCID 68406993, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using an analogous procedure to that described in Method 4, N-(2-t-butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Method 13, 219 mg, 0.5 mmol) was reacted with (2-chloro-1,3-thiazol-5-yl)methyl cyclohexylcarbamate (138 mg, 0.5 mmol). The crude residue was stirred in ethyl acetate for 16 hours before being filtered, mixed with water and the aqueous removed using a Varian Chem Elut Column (CE1010). The resulting solution was concentrated and purified by flash chromatography on silica, eluting with methanol/dichloromethane (0-30%) to give the title compound; Mass Spectrum: M+H+ 551.

Workup

  1. filtrationbefore being filtered
  2. additionmixed with water
  3. customthe aqueous removed
  4. concentrationThe resulting solution was concentrated
  5. custompurified by flash chromatography on silica
  6. washeluting with methanol/dichloromethane (0-30%)

Sources & evidence

ORD record
ord-d53ad154e2594bd6b29b768f5c9e49c7
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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