Dichloromethane → HCID 53497470, compound

HRID 1853023Notes

Reaction equation

HRID 1853023 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.C(Cl)Cl.C(N(CC)CC)C.[CH3:39][CH:40]([S:42](Cl)(=[O:44])=[O:43])[CH3:41]>CCOC(C)=O>[CH:40]([S:42]([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:44])=[O:43])([CH3:41])[CH3:39]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 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 53497470HCID 53497470, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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; 7.1 mg, 0.016 mmol) was suspended in DCM (90 μL, 0.018 mmol) and cooled in an ice bath. To this was added triethylamine (7.5 μL, 0.054 mmol) followed by propane-2-sulfonyl chloride (2.7 mg, 0.019 mmol). The reaction mixture was allowed to warm to ambient temperature. After 15 hours, the reaction mixture was diluted in EtOAc and washed with water and brine. The organic layer was dried with MgSO4, filtered and concentrated down to afford 2-(1-(isopropylsulfonyl)-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile (4.8 mg, 0.010 mmol, 58% yield) as a light yellow oil. MS (apci) m/z=466.6 (M+H).

Workup

  1. temperaturecooled in an ice bath
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated down

Sources & evidence

ORD record
ord-6e9f99e38bdf4b8b929d4e911b1d45ee
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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