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2-Aminoadamantane hydrochloride → 1-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12835
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HRID 12835 반응식
[CH:1]1([N:4]2[C:8]([C:9]([F:12])([F:11])[F:10])=[C:7]([C:13]([OH:15])=O)[CH:6]=[N:5]2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[NH2:46][CH:47]1[CH:54]2[CH2:55][CH:50]3[CH2:51][CH:52]([CH2:56][CH:48]1[CH2:49]3)[CH2:53]2>ClCCl.CN(C=O)C.O>[CH:48]12[CH2:56][CH:52]3[CH2:51][CH:50]([CH2:55][CH:54]([CH2:53]3)[CH:47]1[NH:46][C:13]([C:7]1[CH:6]=[N:5][N:4]([CH:1]3[CH2:2][CH2:3]3)[C:8]=1[C:9]([F:10])([F:11])[F:12])=[O:15])[CH2:49]2
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참가 물질

8

반응물 4

HCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 589728211-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid2회

생성물 1

HCID 250135481-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide
수율 56.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

1-Cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (Intermediate 6, 20 mg, 0.09 mmol) was dissolved in a mixture of dry dichloromethane (1.6 mL) and dry DMF (0.2 mL). DIPEA (0.1 mL, 0.57 mmol) and TSTU (33 mg, 0.11 mmol) were added to the above mixture. After the mixture was stirred for 1 h, the appearance of active ester was detected by LC-MS. Then 2-aminoadamantane hydrochloride (17 mg, 0.09 mmol) was added. After another 2 hours water was added and the organic layer was separated. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were dried under vacuum and purified by silica chromatography eluting with a gradient of 0-40% ethyl acetate/hexanes, then 40% ethyl acetate/hexanes to give 1-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (18 mg, 56%). Mass spectrum: m/z: 354.2 (M+1).

후처리

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. customThe combined organic layers were dried under vacuum
  4. custompurified by silica chromatography
  5. washeluting with a gradient of 0-40% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-4f6a0d022ce842589a91c7fec504bf5e
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728029B2

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