Hydrochloric Acid → HCID 86637285, compound

HRID 1876851Notes

Reaction equation

HRID 1876851 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:24][C:25]#[N:26])[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1.Cl.C(N(CC)CC)C.[CH:35]1([S:38](Cl)(=[O:40])=[O:39])[CH2:37][CH2:36]1>O1CCOCC1.C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:24][C:25]#[N:26])[CH2:14][N:15]([S:38]([CH:35]4[CH2:37][CH2:36]4)(=[O:40])=[O:39])[CH2:16]3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 86637286HCID 86637286, compound

Product 1

HCID 86637285HCID 86637285, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of tert-butyl 3-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-(cyanomethyl)azetidine-1-carboxylate (0.241 g, 0.643 mmol) in 2 mL of dioxane was added 4 M HCl in dioxane (4.0 mL). The reaction was stirred at room temperature for 30 min, then evaporated to dryness. To the resulting crude HCl salt in methylene chloride (5.0 mL) was added triethylamine (0.269 mL, 1.93 mmol) followed by cyclopropanesulfonyl chloride (0.0786 mL, 0.771 mmol). The mixture was stirred at room temperature for 30 min, washed with saturated sodium bicarbonate, dried, and evaporated to dryness. The residue was used directly in next step (229 mg, 94%). LCMS (M+H) 379.0.

Workup

  1. customevaporated to dryness
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. washwashed with saturated sodium bicarbonate
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-858b60b5f5dc4f6f9491493d366ee9d7
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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