Cyclopropanemethanamine, N-propyl- → 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid cyclopropylmethylpropylamide

HRID 916219

反応式

HRID 916219 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([C:20]([OH:22])=O)[N:17]([CH3:19])[N:18]=[C:11]12.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:46]([NH:49][CH2:50][CH:51]1[CH2:53][CH2:52]1)[CH2:47][CH3:48]>ClCCl.C(N(CC)CC)C>[CH:51]1([CH2:50][N:49]([CH2:46][CH2:47][CH3:48])[C:20]([C:16]2[N:17]([CH3:19])[N:18]=[C:11]3[C:12]=2[CH2:13][CH2:14][CH2:15][N:10]3[C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[Cl:1])=[O:22])[CH2:53][CH2:52]1

参加物

7

反応物 4

HCID 117787Cyclopropanemethanamine, N-propyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 221362637-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid

生成物 1

HCID 221362777-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid cyclopropylmethylpropylamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

7-(2-Chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (107.0 mg), 1-hydroxybenzotriazole hydrate (50.3 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (72.5 mg), triethylamine (93 μL), and N-propylcyclopropanemethylamine (49 μL) were combined in 4 mL of dichloromethane and stirred at room temperature over night. The reaction mixture was then partitioned between ethyl acetate and 1M hydrochloric acid. The ethyl acetate solution was washed with aqueous sodium bicarbonate, dried with magnesium sulfate, and concentrated. The crude product was chromatographed on silica gel eluting with an acetone/hexane gradient giving a solid. Recrystallization from hexane provided 75.6 mg of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-carboxylic acid cyclopropylmethylpropylamide, mp 120.6-122.0° C.

後処理

  1. customThe reaction mixture was then partitioned between ethyl acetate and 1M hydrochloric acid
  2. washThe ethyl acetate solution was washed with aqueous sodium bicarbonate
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel eluting with an acetone/hexane gradient
  6. customgiving a solid
  7. customRecrystallization from hexane

出典と根拠

ORDレコード
ord-4993b9d938a34f1ab56e3ad55fd0f04b
出典データセット
uspto-grants-2007_09
特許番号
US07268146B2

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