Tert-Butylamine → HCID 67954714, compound

HRID 2088899Notes

Reaction equation

HRID 2088899 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10]=[C:9]1[CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[C:24]3[C@H:32]([CH3:33])[CH2:31][C:30](=[O:34])[NH:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:19][CH2:18]1)(=O)=O.[C:35]([NH2:39])([CH3:38])([CH3:37])[CH3:36].C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O.[Cl-].[Na+]>[C:35]([NH:39][CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]([F:15])([F:14])[F:16])[N:10]=[C:9]1[CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[C:24]3[C@H:32]([CH3:33])[CH2:31][C:30](=[O:34])[NH:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:19][CH2:18]1)([CH3:38])([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86666574HCID 86666574, compound

Product 1

HCID 67954714HCID 67954714, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Add (R)-2-(2-(1-(5-methyl-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-4-yl)piperidin-4-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl)ethyl methanesulfonate (0.50 g, 0.99 mmol), tert-butylamine (0.52 mL, 7.1 eq), and triethylamine (0.69 mL, 5.0 eq) in dimethylformamide (5 mL). Heat to 50° C. in a sealed tube for 48 hours. Dilute the solution with saturated aqueous sodium chloride. Add the mixture into ethyl acetate. Wash the organics with saturated aqueous sodium chloride and concentrate in vacuo. Purify by silica gel chromatography, eluting with 20% ethanol/acetone, to give the title compound (0.27 g, 55%). MS (ES) m/z=480 [M]+.

Workup

  1. washWash the organics with saturated aqueous sodium chloride
  2. concentrationconcentrate in vacuo
  3. customPurify by silica gel chromatography
  4. washeluting with 20% ethanol/acetone

Sources & evidence

ORD record
ord-aae575e590924d19a23a4bec620038d0
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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