Diisopropylethylamine → HCID 68230800, compound

HRID 1853060Notes

Reaction equation

HRID 1853060 reaction equation
[C:1]([CH2:3][C:4]1([N:15]2[CH:19]=[C:18]([C:20]3[N:25]4[CH:26]=[CH:27][N:28]=[C:24]4[CH:23]=[C:22]([C:29]4[CH:30]=[N:31][C:32]([O:35][CH3:36])=[N:33][CH:34]=4)[N:21]=3)[CH:17]=[N:16]2)[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)#[N:2].Cl.O1CCOCC1.C(N(C(C)C)CC)(C)C.[CH:53]1([S:56](Cl)(=[O:58])=[O:57])[CH2:55][CH2:54]1>CO.ClCCl>[CH:53]1([S:56]([N:6]2[CH2:5][C:4]([CH2:3][C:1]#[N:2])([N:15]3[CH:19]=[C:18]([C:20]4[N:25]5[CH:26]=[CH:27][N:28]=[C:24]5[CH:23]=[C:22]([C:29]5[CH:30]=[N:31][C:32]([O:35][CH3:36])=[N:33][CH:34]=5)[N:21]=4)[CH:17]=[N:16]3)[CH2:7]2)(=[O:58])=[O:57])[CH2:55][CH2:54]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 204431481,4-Dioxane hydrochlorideHCID 86685329HCID 86685329, compound

Product 1

HCID 68230800HCID 68230800, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

tert-Butyl 3-(cyanomethyl)-3-(4-(7-(2-methoxypyrimidin-5-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate (150 mg, 0.308 mmol) was dissolved in MeOH (5 ml) and a 4M HCl/dioxane solution (5 mL) was added. The resulting mixture was stirred for 20 minutes and then was concentrated to a solid. To the solid was added dichloromethane (15 mL) and diisopropyl ethylamine (787 μL, 4.52 mmol). After 10 minutes, the resulting mixture was cooled to −40° C. and cyclopropanesulfonyl chloride (43.3 mg, 0308 mmol) was added. The reaction mixture was allowed to come to ambient temperature overnight. The resulting mixture was concentrated to an oil and the oil was chromatographed to yield 70.8 mg (46.8%) of the title compound. MS (apci) m/z=509.0 (M+H).

Workup

  1. concentrationwas concentrated to a solid
  2. waitAfter 10 minutes
  3. waitto come to ambient temperature overnight
  4. concentrationThe resulting mixture was concentrated to an oil
  5. customthe oil was chromatographed

Sources & evidence

ORD record
ord-c27827da99964272a116584fd3428928
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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