3-Aminobiphenyl → HCID 58709992, compound

HRID 2375853Notes

Reaction equation

HRID 2375853 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21](Cl)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=1>C(O)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:30][C:26]4[CH:25]=[C:24]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH:29]=[CH:28][CH:27]=4)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 167173-AminobiphenylHCID 58709797tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 58709992HCID 58709992, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (60.0 mg, 0.179 mmol) and biphenyl-3-ylamine (30.5 mmol, 0.180 mmol) in nBuOH (3 mL) was heated to 80° C. (bath temp.) for 17 h. The solvent was evaporated, water/NaHCO3 solution was added, the mixture was extracted with CH2Cl2 (3×20 mL), and the combined extracts were washed with brine and dried over MgSO4. MgSO4 was filtered off, the filtrate was concentrated, and the residue was chromatographed on silica gel [Jones Flashmaster, 5 g/25 mL cartridge, eluting with CH2Cl2 (1-9)→1% MeOH in CH2Cl2 (10-19)→2% MeOH in CH2Cl2 (20-30)]. Fr.17-26 were combined and dried in vacuo overnight. One obtained the title compound as off-white solid. MS (ES+): m/z 468.1 (100) [MH+]. HPLC: tR=3.2 min (ZQ2000, nonpolar—5 min). 1H NMR (CDCl3, 400 MHz): δ=1.50 (s, 9H), 2.44-2.55 (brs, 2H), 3.61-3.71 (m, 2H), 4.13-4.22 (m, 2H), 6.15 (s, 1H), 6.24 (s, 1H), 7.11 (brs, 1H), 7.37 (t, J=7.4 Hz, 1H), 7.40-7.52 (m, 4H), 7.60-7.67 (m, 3H), 7.80 (t, J=1.6 Hz, 1H), 8.43 (s, 1H), 11.83 (brs, 1H).

Workup

  1. customThe solvent was evaporated
  2. additionwater/NaHCO3 solution was added
  3. extractionthe mixture was extracted with CH2Cl2 (3×20 mL)
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationMgSO4 was filtered off
  7. concentrationthe filtrate was concentrated
  8. customthe residue was chromatographed on silica gel [Jones Flashmaster, 5 g/25 mL cartridge
  9. washeluting with CH2Cl2 (1-9)
  10. customdried in vacuo overnight

Sources & evidence

ORD record
ord-c18179cd84734b1c9adb4d0938614f0c
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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