Water → HCID 22128981, compound

HRID 1858363Notes

Reaction equation

HRID 1858363 reaction equation
[NH2:1][C:2]1[C:29]([NH2:30])=[CH:28][CH:27]=[CH:26][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:14][CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:8](=[O:13])[C:9]([F:12])([F:11])[F:10].O.[O:32]1CCC[CH2:33]1>>[F:12][C:9]([F:10])([F:11])[C:8]([N:7]([CH2:14][CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[CH2:6][CH2:5][O:4][C:3]1[C:2]2[NH:1][C:33](=[O:32])[NH:30][C:29]=2[CH:28]=[CH:27][CH:26]=1)=[O:13]

Participants

4

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 22128977HCID 22128977, compound

Product 1

HCID 22128981HCID 22128981, compoundYield 82.9%

Conditions

Temperature
23 °C

Procedure

A mixture of N-[2-(2,3-diamino-phenoxy)-ethyl]-2,2,2-trifluoro-N-[3-(1H-indol-3-yl)-propyl]-acetamide (0.5 g, 1.19 mmol) and diimidazole carbonyl (0.39 g, 2.38 mmol) in anhydrous tetrahyrofuran (50 ml) was stirred at 23° C. for 5 hours. The reaction mixture was poured into water and extracted with ethyl acetate (2×250 ml). The organic layer was washed with water (2×250 ml) and brine (200 ml) and dried over anhydrous magnesium sulfate. The resulting product was concentrated to give the crude product. Purification by chromatography (60% ethyl acetate-hexanes) followed by crystallization from ethyl acetate-hexanes afforded 0.44 g (82.9%) of product as yellowish colored solid: mp 180-181° C.; MS EI m/e 446 (M+).

Workup

  1. extractionextracted with ethyl acetate (2×250 ml)
  2. washThe organic layer was washed with water (2×250 ml) and brine (200 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe resulting product was concentrated
  5. customto give the crude product
  6. customPurification by chromatography (60% ethyl acetate-hexanes)
  7. customfollowed by crystallization from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-5eae266bf7284d498b131ce18debce30
Source dataset
uspto-grants-2000_11
Patent number
US06150533

Reaction notes

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