반응식
[CH3:1][N:2]1[C:6]([N:7]2[CH:11]=[CH:10][CH:9]=[N:8]2)=[C:5]([C:12]([OH:14])=O)[CH:4]=[N:3]1.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[NH2:45][CH:46]1[CH:53]2[CH2:54][CH:49]3[CH2:50][CH:51]([CH2:55][CH:47]1[CH2:48]3)[CH2:52]2>ClCCl.CN(C=O)C.O>[CH:47]12[CH2:55][CH:51]3[CH2:50][CH:49]([CH2:54][CH:53]([CH2:52]3)[CH:46]1[NH:45][C:12]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[N:7]1[CH:11]=[CH:10][CH:9]=[N:8]1)=[O:14])[CH2:48]2참가 물질
반응물 4
생성물 1
시약·촉매·용매 3
실험 절차
2′-Methyl-2′H-[1,3′]bipyrazolyl-4′-carboxylic acid (Intermediate 8, 50 mg, 0.26 mmol) was dissolved in a mixture of dry dichloromethane (3.2 mL) and dry DMF (0.8 mL). DIPEA (0.23 mL, 1.3 mmol) and TSTU (93 mg, 0.28 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 (58 mg, 0.31 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 phases were dried under vacuum and purified by C-18 reversed phase prep-HPLC with a gradient of 10-100% acetonitrile/water to give 2′-methyl-2′H-[1,3′]bipyrazolyl-4′-carboxylic acid adamantan-2-ylamide (65 mg, 77%). Mass spectrum: m/z: 362.2 (M+1).
후처리
- customthe organic layer was separated
- extractionThe aqueous layer was extracted twice with dichloromethane
- customThe combined organic phases were dried under vacuum
- custompurified by C-18
출처 및 근거
- ORD 기록
- ord-e39314f40e6043cb9d02def678859e3f
- 출처 데이터셋
- uspto-grants-2010_06
- 특허 번호
- US07728029B2
연결된 노트
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