Water → HCID 86760999, compound

HRID 1437646Notes

Reaction equation

HRID 1437646 reaction equation
Cl.[CH:2]([C@H:15]1[C@@H:20]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)[CH2:19][CH2:18][NH:17][CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[CH3:38][N:39]([CH3:44])[CH2:40][C:41](O)=[O:42].CCN=C=NCCCN(C)C.Cl.O>CN(C=O)C.CCN(CC)CC>[CH:2]([C@H:15]1[C@@H:20]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:26]=[C:25]([C:33]([F:36])([F:34])[F:35])[CH:24]=2)[CH2:19][CH2:18][N:17]([C:41](=[O:42])[CH2:40][N:39]([CH3:44])[CH3:38])[CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 75605N,N-Dimethylglycine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86760996HCID 86760996, compound

Product 1

HCID 86760999HCID 86760999, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of the compound (31.8 mg) obtained in Example 25 in DMF (2.0 ml), Et3N (25.1 μl ) was added, N,N-dimethylglycine hydrochloride (16.7 mg) and WSC.HCl (23 mg) were added thereto and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water, and then the product was extracted with ethyl acetate. The organic layer was washed with an aqueous 10% citric acid solution and saturated brine, and dried, and the solvent was evaporated under reduced pressure, and then the residue was purified by preparative HPLC. The obtained compound was dissolved in ethyl acetate, washed with an aqueous saturated sodium hydrogen carbonate solution and brine, dried, and then the solvent was evaporated under reduced pressure to obtain the title compound.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous 10% citric acid solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by preparative HPLC
  6. dissolutionThe obtained compound was dissolved in ethyl acetate
  7. washwashed with an aqueous saturated sodium hydrogen carbonate solution and brine
  8. customdried
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9536703452254e37abddb1ea84061bb5
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

Loading…