Methylamine → HCID 21104328, compound

HRID 1354338Notes

Reaction equation

HRID 1354338 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[C:20]([C:21](O)=[O:22])=[CH:19][N:18]=[CH:17][CH:16]=3)[C:11]3[CH:24]([CH3:27])[CH2:25][CH2:26][C:10]=3[N:9]=2)[CH:7]=1.[CH2:29]([N:31](CC)CC)C.CN.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[C:20]([C:21]([NH:31][CH3:29])=[O:22])=[CH:19][N:18]=[CH:17][CH:16]=3)[C:11]3[CH:24]([CH3:27])[CH2:25][CH2:26][C:10]=3[N:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 2724699PyBOPHCID 21104327HCID 21104327, compound

Product 1

HCID 21104328HCID 21104328, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 4-[2-(5-chloro-2-fluorophenyl)-5-methyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-nicotinic acid (20 mg, 0.05 mmol, 1 eq) in DMF (2 ml) was added triethylamine (8 μl, 0.05 mmol, 1.1 eq) followed by methylamine (250 μl, 3.89 mmol, 2M solution in THF, 10 eq). To the suspension was added a solution of PyBOP (40 mg, 0.08 mmol, 1.5 eq) in DMF (1 ml) dropwise. The reaction mixture was stirred at room temperature for 16 h. The reaction was concentrated in vacuo and the residue was triturated with ether (2×20 ml). The crude residue was purified by flash column chromatography (100% ethylacetate) to afford 4-[2-(5-chloro-2-fluorophenyl)-5-methyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-N-methyl-nicotinamide, 47 (12 mg, 58%) as a white solid.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was triturated with ether (2×20 ml)
  3. customThe crude residue was purified by flash column chromatography (100% ethylacetate)

Sources & evidence

ORD record
ord-3ceb14f131b6448d833752a1622a7802
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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