Bromine → HCID 54514076, compound

HRID 566724Notes

Reaction equation

HRID 566724 reaction equation
[Br:1]Br.[NH2:3][C@@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:10]=[CH:9][N:8]=1>C(Cl)(Cl)Cl>[NH2:3][C@@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:10]([Br:1])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 54509656HCID 54509656, compound

Product 1

HCID 54514076HCID 54514076, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Bromine (757 mg, 4.7 mmole) in CHCl3 (10 mL) was added in one portion to a stirring solution of 2-((S)-2-amino-3-phenylpropylamino)-4-(4-pyridyl)pyridine (1.44 g, 4.7 mmole) in CHCl3 (30 mL) at room temperature. After 1 hr, the mixture was partitioned between dichloromethane and aqueous sodium bicarbonate. The organic solvent was washed with brine, dried and evaporated. The residue was purified on a column of silica gel (CH2Cl2-MeOH-Conc. NH4OH=1000:110:8). MS (m/z): Calcd. C19H19N4Br (M+): 383, found: 383, 385.1. 1H-NMR (CDCl3, 400 MHz) δ: 8.62(d, 2H), 8.20(s, 1H), 7.30-7.10(m, 7H), 6.32(s, 1H), 5.78(bs, 1H), 3.70-3.30(m, 3H), 2.97(dd, 1H), 2.92(dd, 1H).

Workup

  1. customthe mixture was partitioned between dichloromethane and aqueous sodium bicarbonate
  2. washThe organic solvent was washed with brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified on a column of silica gel (CH2Cl2-MeOH-Conc. NH4OH=1000:110:8)

Sources & evidence

ORD record
ord-c8385a2e674e49ebb735562058af1725
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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