Diisopropylethylamine → 5-bromo-N-(5-(4-methoxyphenyl)-1H-pyrazol-3-yl)pentanamide

HRID 1695203노트

반응식

HRID 1695203 반응식
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:21][N:20]=[C:19]([NH2:22])[CH:18]=2)=[CH:13][CH:12]=1.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[NH:21][N:20]=[C:19]([NH:22][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[CH:18]=2)=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 5211735-Bromovaleryl chlorideHCID 27564693-Amino-5-(4-methoxyphenyl)pyrazole

생성물 1

HCID 577800445-bromo-N-(5-(4-methoxyphenyl)-1H-pyrazol-3-yl)pentanamide수율 85%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

실험 절차

A solution of 5-bromovaleryl chloride (2.1 mL, 15.7 mmol, 1 eq) in dry DMA (35 mL) was cooled to −10° C. (ice/water bath) under N2; a solution of 5-(4-methoxy-phenyl)-1H-pyrazol-3-ylamine (3.0 g, 15.7 mmol, 1 eq) and diisopropylethylamine (2.74 mL, 15.7 mmol, 1 eq) in dry DMA (15 mL) was added over 30 min. After 2 hrs at −10° C., LC-MS shows completion of the reaction which was quenched by addition of H2O (ca. 50 mL). The solid which precipitates was filtered and washed with Et2O, to give 4.68 g of 5-bromo-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-amide as a white powder (13.3 mmol, 85% yield).

후처리

  1. customcompletion of the reaction which
  2. customwas quenched by addition of H2O (ca. 50 mL)
  3. customThe solid which precipitates
  4. filtrationwas filtered
  5. washwashed with Et2O

출처 및 근거

ORD 기록
ord-694a8c96c0714925a961e4c66ea3705b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163729B2

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