Cyclohexane → HCID 73054312, compound

HRID 1778961Notes

Reaction equation

HRID 1778961 reaction equation
[NH2:1][C:2](=[O:41])[CH2:3][C:4]1[CH:40]=[CH:39][CH:38]=[CH:37][C:5]=1[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][N:24](C(OCC4C=CC=CC=4)=O)[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[N:9]=1.C1CCCCC1>CN(C=O)C.C(Cl)Cl.[Pd]>[N:21]1([C:18]2[CH:17]=[CH:16][C:15]([NH:14][C:10]3[N:9]=[C:8]([CH2:7][CH2:6][C:5]4[CH:37]=[CH:38][CH:39]=[CH:40][C:4]=4[CH2:3][C:2]([NH2:1])=[O:41])[CH:13]=[CH:12][N:11]=3)=[CH:20][CH:19]=2)[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]1

Participants

6

Reactant 2

HCID 8078CyclohexaneHCID 86712630HCID 86712630, compound

Product 1

HCID 73054312HCID 73054312, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate (A6) (73 mg, 0.13 mmol) in DMF (5 mL) under nitrogen, was added a slurry of 10% Pd/C (20 mg) in DMF. The resulting mixture was stirred under an atmosphere of hydrogen at room temperature for 19 hours then filtered through a 2.0 PFTE filter. The filtrate was evaporated in vacuo and the residue was loaded onto a SCX (5 g) column using MeOH. The column was washed with 2 column volumes of MeOH followed by 3 column volumes of 1% MeNH2 in MeOH. The 1% MeNH2 in MeOH filtrate was evaporated in vacuo to give a pale brown oil which was taken up in DCM (0.5 mL) and cyclohexane (1 mL) and sonicated. The resulting precipitate was filtered and the filter cake dried in vacuo to give the title compound 1 as a white solid (1.4 mg, 90% purity). 1H-NMR: (400 MHz, d4-MeOH) δ 8.22-8.16 (m, 1H), 7.57-7.48 (m, 2H), 7.20 (m, 4H), 7.01-6.93 (m, 2H), 6.60 (dd, J=5.0, 2.8 Hz, 1H), 3.63 (d, J=2.3 Hz, 2H), 3.18-3.12 (m, 4H), 3.09 (dd, J=9.2, 6.4 Hz, 5H), 2.93-2.83 (m, 3H). LC-MS Method A: rt 4.305 min; m/z 417.2 [m+H]+.

Workup

  1. filtrationthen filtered through a 2.0 PFTE
  2. filtrationfilter
  3. customThe filtrate was evaporated in vacuo
  4. washThe column was washed with 2 column volumes of MeOH
  5. customThe 1% MeNH2 in MeOH filtrate was evaporated in vacuo
  6. customto give a pale brown oil which
  7. filtrationThe resulting precipitate was filtered
  8. customthe filter cake dried in vacuo

Sources & evidence

ORD record
ord-48018324d6754cb4b465b970e63899f0
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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