Water → HCID 18700278, compound

HRID 2288631Notes

Reaction equation

HRID 2288631 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[Cl:13][C:14]1[C:15]([O:25][CH:26]([CH3:30])[C:27]([OH:29])=O)=[N:16][C:17]([CH3:24])=[N:18][C:19]=1[C:20]([F:23])([F:22])[F:21].[NH2:31][C:32]([CH3:39])([C:35]([CH3:38])([CH3:37])[CH3:36])[C:33]#[N:34].O>O1CCCC1>[Cl:13][C:14]1[C:15]([O:25][CH:26]([CH3:30])[C:27]([NH:31][C:32]([C:33]#[N:34])([CH3:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:29])=[N:16][C:17]([CH3:24])=[N:18][C:19]=1[C:20]([F:21])([F:22])[F:23]

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 156833752-Amino-2,3,3-trimethylbutanenitrileHCID 18700273HCID 18700273, compound

Product 1

HCID 18700278HCID 18700278, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodimide hydrochloride (0.8 g) was added to a solution containing 2-(5-chloro-2-methyl-6-trifluoromethylpyrimidin-4-yloxy)propionic acid (1.0 g) dissolved in tetrahydrofuran (30 ml), at room temperature, and the mixture was stirred for 30 min. Subsequently, 2-amino-2,3,3-trimethylbutyronitrile (0.5 g) was added to the mixture, and the reaction mixture was stirred for 10 hours at room temperature. After completion of the reaction, water was added to the resulting mixture and the organic layer was extracted with ethyl acetate, and subsequently dried over anhydrous magnesium sulfate. The ethyl acetate was removed under reduced pressure. The residue was purified by column chromatography on silica gel to give 0.3 g of the A-configurational diastereomer having a melting point of 1 33° C. to 1 34° C. and 0.2 g of the B-configurational diastereomer having a melting point of 137° C. to 139° C.

Workup

  1. stirringthe reaction mixture was stirred for 10 hours at room temperature
  2. additionwas added to the resulting mixture
  3. extractionthe organic layer was extracted with ethyl acetate
  4. dry with materialsubsequently dried over anhydrous magnesium sulfate
  5. customThe ethyl acetate was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. customto give 0.3 g of the A-configurational diastereomer
  8. customa melting point of 1 33° C.
  9. customto 1 34° C. and 0.2 g of the B-configurational diastereomer

Sources & evidence

ORD record
ord-dbe0c2f67e2d48a6be49176ae5c4a417
Source dataset
uspto-grants-2000_07
Patent number
US06090815

Reaction notes

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