Cyanuric chloride → HCID 9933767, compound

HRID 1937808Notes

Reaction equation

HRID 1937808 reaction equation
N1C(Cl)=NC(Cl)=NC=1Cl.[CH3:10][N:11]([CH3:42])[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C@H:22]([C:27]([NH:29][C:30](=O)[C@H:31](CCC2C=CC=CC=2)[NH2:32])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])(=[O:20])=[O:19])=[CH:14][CH:13]=1.[C:43]([C:46]#N)([CH3:45])=O.O>CN(C=O)C>[C:31]([C@@H:30]([NH:29][C:27](=[O:28])[C@@H:22]([NH:21][S:18]([C:15]1[CH:14]=[CH:13][C:12]([N:11]([CH3:10])[CH3:42])=[CH:17][CH:16]=1)(=[O:20])=[O:19])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:45][CH2:43][C:46]1[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=1)#[N:32]

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 21339348HCID 21339348, compoundHCID 131723227HCID 131723227, compound

Product 1

HCID 9933767HCID 9933767, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyanuric chloride (33 mg, 0.18 mmol) was added to a solution of N-[N-((4-dimethylaminophenyl)sulfonyl)-L-leucinyl]-L-homophenylalaninamide (80 mg, 0.18 mmol) in DMF (2 mL) at 0° C. After stirring for 2h, the reaction was quenched by addition of satd. NaHCO3, filtered, diluted with EtOAc, washed sequentially with H2O (×5), brine, dried over Na2SO4, and concentrated giving a yellow foam. The crude residue was fractionated by preparative HPLC (65% AcCN/H2O/0.1% TFA) giving the title compound (47 mg, 57%) as a white solid, m.p. 46-48° C. 1H NMR (400 MHz, CDCl3): δ: 7.74(2H, d, J=9), 7.37-7.34 (2H, m), 7.30-7.26 (2H, m), 7.23-7.21 (3H, m), 6.79 (1H, d, J=8.5), 4.91 (1H, bs), 4.70 (1H, ddd, J=8, 8, 8), 3.68-3.73 (1H, m), 3.06 (3H, s), 2.84-2.76 (2H, m), 2.16-2.09(2H, m), 1.63-1.56 (2H, m), 1.42-1.37 (1H, m), 0.88 (3H, d, J=6), 0.71 (3H, d, J=6).

Workup

  1. customthe reaction was quenched by addition of satd
  2. filtrationNaHCO3, filtered
  3. additiondiluted with EtOAc
  4. washwashed sequentially with H2O (×5), brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customgiving a yellow foam

Sources & evidence

ORD record
ord-2ca5bf24b62a4060b3376badd5f4f7bc
Source dataset
uspto-grants-2002_05
Patent number
US06395897B1

Reaction notes

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