Diisopropylethylamine → 6-isobutyl-5-methyl-nicotinic acid N'-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide

HRID 2065918노트

반응식

HRID 2065918 반응식
Cl.[CH2:2]([C:6]1[C:14]([CH3:15])=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][N:7]=1)[CH:3]([CH3:5])[CH3:4].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:47]([O:50][C:51]1[C:60]([CH3:61])=[CH:59][C:54]([C:55]([NH:57][NH2:58])=[O:56])=[CH:53][C:52]=1[CH3:62])[CH:48]=[CH2:49]>C(Cl)Cl.CC(=O)OCC>[CH2:47]([O:50][C:51]1[C:60]([CH3:61])=[CH:59][C:54]([C:55]([NH:57][NH:58][C:10](=[O:12])[C:9]2[CH:13]=[C:14]([CH3:15])[C:6]([CH2:2][CH:3]([CH3:4])[CH3:5])=[N:7][CH:8]=2)=[O:56])=[CH:53][C:52]=1[CH3:62])[CH:48]=[CH2:49]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 592020394-Allyloxy-3,5-dimethyl-benzoic acid hydrazideHCID 670271826-Isobutyl-5-methyl-nicotinic acid hydrochloride

생성물 1

HCID 687652896-isobutyl-5-methyl-nicotinic acid N'-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide수율 97.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6-isobutyl-5-methyl-nicotinic acid hydrochloride (50 mg, 0.22 mmol), DIPEA (0.12 mL, 0.7 mmol) and TBTU (97 mg, 0.30 mmol) in DCM (5 mL) is added at 0° C. 4-allyloxy-3,5-dimethyl-benzoic acid hydrazide (50.6 mg, 0.23 mmol) and the mixture is stirred at 0° C. for 4 h. The mixture is diluted with EA (15 mL) and washed with 1M aq. NaH2PO4 (5 mL), 1M aq. NaOH (5 mL) and water (5 mL). The org. phase is dried (MgSO4), filtered and evaporated to provide 6-isobutyl-5-methyl-nicotinic acid N′-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide (85 mg); LC-MS: tR=0.81 min, [M+1]+=396.20.

후처리

  1. washwashed with 1M aq. NaH2PO4 (5 mL), 1M aq. NaOH (5 mL) and water (5 mL)
  2. dry with materialphase is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-523c4908a0b248f2a27898e77dab6b7c
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288554B2

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