Ethyl Acetate → HCID 71668135, compound

HRID 624672Notes

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]

Participants

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

temperatureAfter cooling to room temperature
filtrationthen filtered through a pad of Celite
washThe combined filtrate is washed with brine
dry with materialthe organic layer is dried over Na2SO4
customAfter the removal of EtOAc in vacuo
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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