Hydrochloric Acid → HCID 58092783, compound

HRID 1807677Notes

Reaction equation

HRID 1807677 reaction equation
[CH:1]1([CH2:4][C:5]2[S:6][C:7]3[CH2:20][CH2:19][C:11]4[N:12]=[C:13]([NH:15]C(=O)C)[S:14][C:10]=4[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.Cl>CCO>[CH:1]1([CH2:4][C:5]2[S:6][C:7]3[CH2:20][CH2:19][C:11]4[N:12]=[C:13]([NH2:15])[S:14][C:10]=4[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86649532HCID 86649532, compound

Product 1

HCID 58092783HCID 58092783, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

N-(7-Cyclopropylmethyl-4,5-dihydro-benzo[1,2-d;3,4-d′]bisthiazol-2-yl)-acetamide (Stage V.2, 180 mg, 0.589 mmol) was dissolved in EtOH (10 mL) and 36% HCl (1.193 g, 11.79 mmol) added. The RM was heated to 90° C. for 16 h then cooled and extracted with EtOAc/H2O. The organic layer was dried over Na2SO4 and evaporated. The crude material was chromatographed with MPLC C18 H2O 0.1% TFA/CH3CN 0.1% TFA, gradient 0-50%. Product containing fractions were neutralized with NaHCO3, extracted with EtOAc and lyophilized from dioxane to give the title compound (M+H=264.2; M−H=262.1; tR 4.183 min (Method F)).

Workup

  1. temperaturethen cooled
  2. extractionextracted with EtOAc/H2O
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated
  5. customThe crude material was chromatographed with MPLC
  6. additionProduct containing fractions
  7. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-125ed3a044e441eaafcc8dc2139344b7
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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