Reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]([OH:11])=O.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[NH2:42][CH:43]1[CH:50]2[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:52][CH:44]1[CH2:45]3)[CH2:49]2>ClCCl.CN(C=O)C.O>[CH:44]12[CH2:52][CH:48]3[CH2:47][CH:46]([CH2:51][CH:50]([CH2:49]3)[CH:43]1[NH:42][C:9]([C:3]1[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=1[Cl:1])=[O:11])[CH2:45]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid (69 mg, 0.4 mmol, CAS#: 27006-82-2, purchased from Maybridge) was dissolved in a mixture of dry dichloromethane (3.2 mL) and dry DMF (0.8 mL). DIPEA (0.28 mL, 1.6 mmol) and TSTU (145 mg, 0.4 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 (75 mg, 0.4 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 HPLC with a gradient of 10-100% acetonitrile/water to give 5-chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (72 mg, 58%). Mass spectrum: m/z: 308.1 (M+1).
Workup
- 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
Sources & evidence
- ORD record
- ord-50e7ad3ab4024b1b8b9a373a9da549ff
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728029B2
Linked notes
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