Piperazine → HCID 22022977, compound

HRID 1793673Notes

Reaction equation

HRID 1793673 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][O:15][C:16]3[CH:20]=[CH:19][O:18][N:17]=3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1F.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][O:15][C:16]3[CH:20]=[CH:19][O:18][N:17]=3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 22022960HCID 22022960, compound

Product 1

HCID 22022977HCID 22022977, compound

Procedure

(5RS)-3-(3,4-Difluorophenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydroisoxazole (530 mg, 1.89 mM) was treated with piperazine using essentially the conditions of Example 4, except that the reaction conditions were 140° for 4 hours, and work-up did not include an acid wash. Crude product was chromatographed on a 50 g silica Mega Bond Elut® column, eluting with a mixture of dichloromethane/methanol/ammonia 90:10:1. Relevant fractions were combined to give the desired product (601 mg). MS (ESP): 347 (MH+) for C17H11FN4O3

Workup

  1. customexcept that the reaction conditions
  2. washwash
  3. customCrude product was chromatographed on a 50 g silica Mega Bond Elut® column
  4. washeluting with a mixture of dichloromethane/methanol/ammonia 90:10:1

Sources & evidence

ORD record
ord-1dc8ffc6324846a7b3c1562422dd92ff
Source dataset
uspto-grants-2006_07
Patent number
US07081538B1

Reaction notes

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