Tyramine → HCID 11045887, compound

HRID 496021Notes

Reaction equation

HRID 496021 reaction equation
NCCC1C=[CH:8][C:7]([OH:10])=[CH:6]C=1.[CH3:11]CN(C(C)C)C(C)C.[Cl:20][C:21]1[N:26]=[C:25]([Cl:27])[N:24]=[C:23]([N:28]([CH2:30][CH2:31]CC2C=CC(F)=CC=2)[CH3:29])[N:22]=1.FC1C=CC(CCCNC)=CC=1.[CH3:52][N:53]([CH:55]=[O:56])C>>[C:7]([O:10][C:55]([N:53]1[CH2:52][CH2:29][N:28]([C:23]2[N:24]=[C:25]([Cl:27])[N:26]=[C:21]([Cl:20])[N:22]=2)[CH2:30][CH2:31]1)=[O:56])([CH3:6])([CH3:8])[CH3:11]

Participants

6

Reactant 5

HCID 5610TyramineHCID 6228Dimethylformamide3×HCID 81531DiisopropylethylamineHCID 110015622,4-Dichloro-6-{[3-(4-fluorophenyl)propyl]methylamino}-1,3,5-triazineHCID 110842664-Fluoro-N-methyl-benzenepropanamine

Product 1

HCID 11045887HCID 11045887, compoundYield 100%

Procedure

A solution of tyramine (302 mg, 2.3 mmol) and DIEA (299 mg, 2.3 mmol) in DMF (5 mL) was added dropwise to a DMF solution (5 mL) of 2,4-dichloro-6-{[3-(4-fluorophenyl)propyl]methylamino}-1,3,5-triazine (prepared in 92% yield via the procedure outlined for the preparation of Intermediate 13, using N-[3-(4-fluorophenyl)propyl]-N-methylamine, Intermediate 5), (714 mg, 2.3 mmol) in DMF (10 mL). The resulting solution was stirred at RT for 2 h. The solvent was removed under reduced pressure and the resulting residue was diluted with EtOAc (80 mL) and washed with 10% aqueous citric acid (2×40 mL). The organic layer was dried over sodium sulfate and concentrated to give the title compound (950 mg, 100%) as a white solid which was used without further purification: 1H NMR (CDCl3, 400 MHz) δ 7.27-6.94 (m, 6H), 6.75 (m, 2H), 5.40-5.32 (d, br, 1H) 3.72-3.56 (m, 4H), 3.11 (m, 3H), 2.78 (m, 2H), 2.62 (m, 2H), 1.92 (m, 2H); Low resolution MS (ES+) m/e 416.4 (MH+). Intermediate 22: tert-butyl 4-(4-{[3-(4-chlorophenyl)propyl]sulfanyl}-6-{[2-(4-hydroxyphenyl)ethyl]amino}-1,3,5-triazin-2-yl)-1-piperazinecarboxylate

Workup

  1. customprepared in 92% yield via the procedure
  2. customThe solvent was removed under reduced pressure
  3. additionthe resulting residue was diluted with EtOAc (80 mL)
  4. washwashed with 10% aqueous citric acid (2×40 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9ce16c11dfac481a8c875b89f2d874c4
Source dataset
uspto-grants-2005_09
Patent number
US06943162B2

Reaction notes

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