Triethylamine → HCID 11681702, compound

HRID 1676893Notes

Reaction equation

HRID 1676893 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])[CH:5]=[CH:6][C:7]=1[F:8].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[CH3:31][N:32]1[CH:36]=[C:35]([C:37](O)=[O:38])[C:34]([CH3:40])=[N:33]1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:37]([C:35]2[C:34]([CH3:40])=[N:33][N:32]([CH3:31])[CH:36]=2)=[O:38])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 12733041,3-dimethyl-1H-pyrazole-4-carboxylic acidHCID 116009993'-chloro-4'-fluoro-2-aminobiphenyl

Product 1

HCID 11681702HCID 11681702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 0.47 g of 3′-chloro-4′-fluoro-2-aminobiphenyl and 0.82 g of bis(2-oxo-3-oxazolidinyl)phosphoryl chloride were added to a solution of 0.30 g of 1,3-dimethyl-1H-pyrazole-4-carboxylic acid and 0.43 g of triethylamine in 30 ml of dichloromethane. The mixture was stirred at room temperature for 12 hours. The mixture was then washed successively twice with dilute hydrochloric acid, twice with aqueous sodium bicarbonate solution and once with water. The organic phase was dried and concentrated. The crude product was purified by silica gel column chromatography using cyclohexane/methyl tert-butyl ether 1:2. This gave 0.56 g of the desired product as white crystals of m.p. 177-180° C.

Workup

  1. washThe mixture was then washed successively twice with dilute hydrochloric acid, twice with aqueous sodium bicarbonate solution and once with water
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d335c10f31e4aeb991df57042f4ce6d
Source dataset
uspto-grants-2011_08
Patent number
US08008232B2

Reaction notes

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