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

HRID 2065918ノート

反応式

HRID 2065918 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-523c4908a0b248f2a27898e77dab6b7c
出典データセット
uspto-grants-2012_10
特許番号
US08288554B2

反応ノート

読み込み中…