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Ethyl Acetate → HCID 71668135, compound

HRID 624672
Notes
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Reaction equation

HRID 624672 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]2[S:33][C:14]3=[N:15][C:16]([N:20]4[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]4)=[CH:17][C:18](=[O:19])[N:13]3[N:12]=2)[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[NH4+:34].[Cl-].[CH3:36][CH2:37][O:38]C(C)=O>CCO.O.[Fe]>[NH2:34][CH2:36][C:37]([NH:8][C:6]1[CH:5]=[C:4]([C:11]2[S:33][C:14]3=[N:15][C:16]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[CH:17][C:18](=[O:19])[N:13]3[N:12]=2)[CH:3]=[C:2]([Br:1])[CH:7]=1)=[O:38]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 89711506HCID 89711506, compound

Product 1

HCID 71668135HCID 71668135, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of tert-butyl 4-(2-(3-bromo-5-nitrophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (460 mg, 0.86 mmol) in EtOH (5 ml) and water (1 ml) are added iron powder (239 mg, 4.38 mmol) and NH4Cl (137 mg, 2.57 mmol) and the mixture is heated at 70° C. for 5 h. After cooling to room temperature, EtOAc (30 ml) is added and the mixture is further stirred for 10 min then filtered through a pad of Celite. The combined filtrate is washed with brine and the organic layer is dried over Na2SO4. After the removal of EtOAc in vacuo, the crude residue is purified by Biotage column chromatography (MeOH/DCM: 1/100 to 1/20 gradient) to give the desired product (380 mg, 88%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthen filtered through a pad of Celite
  3. washThe combined filtrate is washed with brine
  4. dry with materialthe organic layer is dried over Na2SO4
  5. customAfter the removal of EtOAc in vacuo
  6. customthe crude residue is purified by Biotage column chromatography (MeOH/DCM: 1/100 to 1/20 gradient)

Sources & evidence

ORD record
ord-8a200a95632a41a99e819e753e09ea84
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09303044B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes