Hydrochloric Acid → HCID 67487426, compound

HRID 1809636Notes

Reaction equation

HRID 1809636 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[C:10]([NH:22][C:23]3[S:27][N:26]=[C:25]([CH:28]4[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37]C(C)(C)C)=O)[CH2:30][CH2:29]4)[N:24]=3)=[N:11][CH:12]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:14]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:42](O)(C(F)(F)F)=O.C(N(CC)CC)C.C(OC(=O)C)(=O)C.[ClH:63]>C(Cl)Cl>[ClH:63].[ClH:63].[CH3:1][C:2]1[C:7]([O:8][C:9]2[C:10]([NH:22][C:23]3[S:27][N:26]=[C:25]([CH:28]4[CH2:34][CH2:33][CH2:32][N:31]([C:35](=[O:37])[CH3:42])[CH2:30][CH2:29]4)[N:24]=3)=[N:11][CH:12]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:14]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68705716HCID 68705716, compound

Product 1

HCID 67487426HCID 67487426, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)azepane-1-carboxylate (70.4 mg, 0.119 mmol) was dissolved in CH2Cl2 (2 mL) and TFA (2 mL) was added. After 10 minutes the reaction was concentrated and placed on high vacuum pump to remove excess TFA. The residue was dissolved in CH2Cl2 (2 mL) and triethylamine (82.3 μL, 0.591 mmol) and acetic anhydride (16.7 μL, 0.177 mmol) were added. After 10 minutes the reaction was partitioned between saturated aqueous NaHCO3 and EtOAc, dried over sodium sulfate, filtered and concentrated. The residue was purified over silica gel (10% methanol in EtOAc) to afford 1-(4-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)azepan-1-yl)ethanone dihydrochloride (68.2 mg, 0.112 mmol, 95.2% yield) as a solid after HCl salt formation. Mass spectrum (apci) m/z=534.2 (M+H-2HCl).

Workup

  1. concentrationAfter 10 minutes the reaction was concentrated
  2. customto remove excess TFA
  3. dissolutionThe residue was dissolved in CH2Cl2 (2 mL)
  4. customAfter 10 minutes the reaction was partitioned between saturated aqueous NaHCO3 and EtOAc
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified over silica gel (10% methanol in EtOAc)

Sources & evidence

ORD record
ord-436f1fb73ec248c4946a9d293b963142
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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