HCID 57461728, compound → HCID 58235131, compound

HRID 1896663Notes

Reaction equation

HRID 1896663 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[N:13]([CH:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[CH:12]=[N:11][C:10]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][N:4]=1.C1(C2N=CN(C3CCNCC3)C=2C2C=CN=CN=2)C=CC=CC=1>>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[N:13]([CH:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[CH:12]=[N:11][C:10]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 57461728HCID 57461728, compoundHCID 58235109tert-Butyl 4-{5-[2-(methylamino)pyrimidin-4-yl]-4-phenyl-1H-imidazol-1-yl}piperidine-1-carboxylate

Product 1

HCID 58235131HCID 58235131, compound

Procedure

The title compound was prepared from tert-butyl 4-{5-[2-(methylamino)pyrimidin-4-yl]-4-phenyl-1H-imidazol-1-yl}piperidine-1-carboxylate (C25) according to the general procedure for the synthesis of 4-(4-phenyl-1-piperidin-4-yl-1H-imidazol-5-yl)pyrimidine (C23) in Example 11. In this case, after the organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure, the product was obtained as a white solid. Yield: 174 mg, 0.520 mmol, 100%. APCI m/z 335.0 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.09-2.20 (m, 2H), 2.37 (br d, J=12 Hz, 2H), 2.97 (s, 3H), 3.0-3.04 (m, 2H), 3.41-3.46 (m, 2H), 4.93 (tt, J=12, 4 Hz, 1H, assumed; partially obscured by water signal), 6.33 (d, J=5.1 Hz, 1H), 7.27-7.35 (m, 3H), 7.37-7.41 (m, 2H), 8.05 (s, 1H), 8.09 (d, J=5.1 Hz, 1H).

Workup

  1. dry with materialIn this case, after the organic layers were dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customthe product was obtained as a white solid

Sources & evidence

ORD record
ord-21a4462289a142f3ac1a8dd1d5b5fc78
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

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