Triethylamine → HCID 44609233, compound

HRID 1963775Notes

Reaction equation

HRID 1963775 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][NH2:9])=[CH:6][C:5]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3[N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:4][N:3]=1.CCN(CC)CC.[C:33](Cl)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH2:8][NH:9][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:6][C:5]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3[N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 44609235HCID 44609235, compound

Product 1

HCID 44609233HCID 44609233, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Some starting materials may be obtained from Adesis Inc., New Castle, Del.) To a mixture of (2-chloro-5-(4-morpholinoquinolin-6-yl)pyridin-3-yl)methanamine (50 mg, 141 μmol) and Et3N (300 μl, 2152 μmol) in DCM (5 mL) was added pivaloyl chloride (100 μL, 813 μmol). The solution was stirred at rt for 1 h. The mixture was partitioned between DCM (10 mL) and aqueous NaHCO3 (20 mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified on silica with 1-5% (2N NH3-MeOH) in DCM to give the product as a yellow solid after concentration (20 mg, 32%). LCMS (ESI, pos. ion): calc'd for C24H27ClN4O2:438.2; found: 439.2 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) d ppm 1.21-1.28 (m, 12 H) 3.19-3.35 (m, 4 H) 3.95-4.08 (m, 4 H) 4.58 (d, J=6.06 Hz, 2 H) 6.37 (br. s., 1 H) 6.93 (d, J=4.89 Hz, 1 H) 7.83 (dd, J=8.90, 1.66 Hz, 1 H) 8.00 (d, J=2.15 Hz, 1 H) 8.10-8.25 (m, 5 H) 8.61 (d, J=2.15 Hz, 2 H) 8.79 (d, J=4.89 Hz, 2 H)

Workup

  1. customThe mixture was partitioned between DCM (10 mL) and aqueous NaHCO3 (20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified on silica with 1-5% (2N NH3-MeOH) in DCM

Sources & evidence

ORD record
ord-47f13a43a8174498852e7847323fb37d
Source dataset
uspto-grants-2013_04
Patent number
US08415376B2

Reaction notes

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