Methanesulfonic Acid → HCID 86594564, compound

HRID 1744103Notes

Reaction equation

HRID 1744103 reaction equation
CS(O)(=O)=O.[C:6]([CH2:8][NH:9][C:10](=[O:41])[C@H:11]([CH2:37][CH:38]([CH3:40])[CH3:39])[NH:12][C:13]1[S:17][N:16]=[CH:15][C:14]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1N1CCN(C(OC(C)(C)C)=O)CC1)#[N:7].[CH2:42]1[CH2:46]OCC1>>[C:6]([CH2:8][NH:9][C:10](=[O:41])[C@H:11]([CH2:37][CH:38]([CH3:39])[CH3:40])[NH:12][C:13]1[S:17][N:16]=[CH:15][C:14]=1[C:18]1[CH:19]=[CH:20][C:21]([N:7]2[CH2:42][CH2:46][NH:9][CH2:8][CH2:6]2)=[CH:22][CH:23]=1)#[N:7]

Participants

4

Reactant 3

HCID 6395Methanesulfonic Acid3×HCID 8028TetrahydrofuranHCID 86594563HCID 86594563, compound

Product 1

HCID 86594564HCID 86594564, compound

Procedure

Methanesulfonic acid (16 μL, 0.24 mmol) was added dropwise over 5 min to a stirred solution of N1-(cyanomethyl)-N2-[4-(4-(tert-butoxycarbonyl)piperazin-1-ylphenyl)isothiazol-5-yl]leucinamide (63 mg, 0.12 mmol) in THF (0.21 mL) at rt. Stirring was continued for 1 h before additional methanesulfonic acid (16 μL, 0.24 mmol) was introduced in the same manner with stirring for 1 h. A final portion of methanesulfonic acid (8 μL, 0.12 mmol) was added dropwise over 3 min and the mixture was stirred at rt for 8 h. The reaction was quenched by the careful addition of an excess of saturated sodium bicarbonate solution. Extraction with ethyl acetate (3×), drying of the combined organics (Na2SO4) and concentration in vacuo gave 48 mg of N1-(cyanomethyl)-N2-[4-(4-piperazin-1-ylphenyl)isothiazol-5-yl]leucinamide as a tan foam. MS (+ESI): 413.2 [M+1]+.

Workup

  1. additionwas introduced in the same manner
  2. stirringwith stirring for 1 h
  3. stirringthe mixture was stirred at rt for 8 h
  4. customThe reaction was quenched by the careful addition of an excess of saturated sodium bicarbonate solution
  5. extractionExtraction with ethyl acetate (3×)
  6. dry with materialdrying of the combined organics (Na2SO4) and concentration in vacuo

Sources & evidence

ORD record
ord-b607ebc3628f4152989b8ac532965f18
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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