Acetic Anhydride → 2-(1-acetyl-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile

HRID 1853013Notes

Reaction equation

HRID 1853013 reaction equation
Cl.[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([C:19]4([CH2:23][C:24]#[N:25])[CH2:22][NH:21][CH2:20]4)[CH:18]=3)[N:11]3[CH:26]=[CH:27][N:28]=[C:10]3[CH:9]=2)[CH:5]=[N:4]1.C1C[O:32][CH2:31][CH2:30]1.C(N(CC)CC)C.C(OC(=O)C)(=O)C>O>[C:31]([N:21]1[CH2:22][C:19]([CH2:23][C:24]#[N:25])([N:17]2[CH:18]=[C:14]([C:12]3[N:11]4[CH:26]=[CH:27][N:28]=[C:10]4[CH:9]=[C:8]([C:6]4[CH:5]=[N:4][N:3]([CH3:2])[CH:7]=4)[N:13]=3)[CH:15]=[N:16]2)[CH2:20]1)(=[O:32])[CH3:30]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 674570102-(3-(4-(7-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride

Product 1

HCID 866853142-(1-acetyl-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrileYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride (Example 62; 20 mg, 0.046 mmol) in THF (460 μL, 0.046 mmol) was added triethylamine (19 μL, 0.14 mmol) and acetic anhydride (5.7 mg, 0.056 mmol). After stirring at ambient temperature for 30 minutes, the reaction mixture was diluted in water. The reaction mixture was directly purified by reverse phase HPLC using a 0-100% acetonitrile/water gradient to afford 2-(1-acetyl-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile (15 mg, 0.038 mmol, 82% yield) as a fluffy white solid. MS (apci) m/z=402.2 (M+H).

Workup

  1. customThe reaction mixture was directly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-db339df9ec0f41a3af9f80b17f03ec5a
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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