Methyl chloroformate → HCID 68512538, compound

HRID 2063258Notes

Reaction equation

HRID 2063258 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]([CH3:33])[CH3:32])[N:25]=3)=[C:18]3[CH2:19][NH:20][CH2:21][CH2:22][N:17]3[N:16]=2)=[CH:11][CH:10]=1.Cl[C:35]([O:37][CH3:38])=[O:36]>O1CCCC1>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]([CH3:33])[CH3:32])[N:25]=3)=[C:18]3[CH2:19][N:20]([C:35]([O:37][CH3:38])=[O:36])[CH2:21][CH2:22][N:17]3[N:16]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 68512581HCID 68512581, compound2×

Product 1

HCID 68512538HCID 68512538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Triethylamine (96 mg, 0.948 mmol) was added to a solution of 4-[2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl]-N-(1-methylethyl)-2-pyrimidinamine (i.e. the product of Step E) (0.150 g, 0.426 mmol) and methyl chloroformate (41.1 μL, 0.178 mmol) in tetrahydrofuran (40 mL). The reaction mixture was stirred at 25° C. for 24 h. The resulting mixture was concentrated under reduced pressure. The residue was diluted with dichloromethane (50 mL) and treated with silica gel (10.0 g). The silica gel suspension was concentrated under reduced pressure to leave a mixture of silica gel and crude product, which was purified by silica gel chromatography using a gradient of ethyl acetate/hexanes (0:1 to 1:4) as eluant to give 25 mg of the title product, a compound of the present invention, as an off-white solid.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with dichloromethane (50 mL)
  3. additiontreated with silica gel (10.0 g)
  4. concentrationThe silica gel suspension was concentrated under reduced pressure
  5. customto leave
  6. additiona mixture of silica gel and crude product, which
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-1b0369509fad4f91a39bca37494c514e
Source dataset
uspto-grants-2012_10
Patent number
US08288375B2

Reaction notes

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