Hydrochloric Acid → HCID 58203698, compound

HRID 1849378Notes

Reaction equation

HRID 1849378 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17]2[S:18][C:19]3[CH2:20][CH2:21][O:22][C:23]4[CH:30]=[C:29]([C:31]5[CH:32]=[N:33][N:34]([CH2:36][C:37]([OH:40])([CH3:39])[CH3:38])[CH:35]=5)[CH:28]=[CH:27][C:24]=4[C:25]=3[N:26]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.[Cl:46]N1C(=O)CCC1=O.Cl>O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([N:12]2[C:16]([Cl:46])=[CH:15][N:14]=[C:13]2[C:17]2[S:18][C:19]3[CH2:20][CH2:21][O:22][C:23]4[CH:30]=[C:29]([C:31]5[CH:32]=[N:33][N:34]([CH2:36][C:37]([OH:40])([CH3:39])[CH3:38])[CH:35]=5)[CH:28]=[CH:27][C:24]=4[C:25]=3[N:26]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 58203701HCID 58203701, compound

Product 1

HCID 58203698HCID 58203698, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-(2-{8-[1-(2-Hydroxy-2-methyl-propyl)-1H-pyrazol-4-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl}-imidazol-1-yl)-azetidine-1-carboxylic acid tert-butyl ester (90.0 mg, 0.179 mmol) in N,N-Dimethylformamide (3.35 mL, 43.3 mmol) was added N-Chlorosuccinimide (19 mg, 0.14 mmol) and 1.00 M of Hydrogen chloride in Water (0.018 mL). The reaction was stirred at rt 4 h. the reaction was quenched with water then extracted with EtOAc 3×. The organic layer was dried Na2SO4, concentrated. The crude product was purified by isco column to give 3-(5-Chloro-2-{8-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-4-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl}-imidazol-1-yl)-azetidine-1-carboxylic acid tert-butyl ester (EtOAc/Hep eluted at 75%). MS: (ESI+)=483.1

Workup

  1. customwas quenched with water
  2. extractionthen extracted with EtOAc 3×
  3. concentrationconcentrated
  4. customThe crude product was purified by isco column

Sources & evidence

ORD record
ord-f216473c64594017932cd7d0b7132f95
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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