Isoamylamine → 6-Cyclobutylmethoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid (3-methyl-butyl)-amide
Reaction equation
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:34]1([CH2:38][O:39][C:40]2[N:45]=[C:44]([C:46]([OH:48])=O)[CH:43]=[N:42][C:41]=2[N:49]2[CH2:53][CH2:52][CH2:51][CH2:50]2)[CH2:37][CH2:36][CH2:35]1.[CH3:54][CH:55]([CH3:59])[CH2:56][CH2:57][NH2:58].C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:54][CH:55]([CH3:59])[CH2:56][CH2:57][NH:58][C:46]([C:44]1[CH:43]=[N:42][C:41]([N:49]2[CH2:53][CH2:52][CH2:51][CH2:50]2)=[C:40]([O:39][CH2:38][CH:34]2[CH2:35][CH2:36][CH2:37]2)[N:45]=1)=[O:48]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of PyBOP (156.1 mg, 0.3 mmol) in N,N-dimethylformamide (0.5 mL) was added to a solution of the 6-cyclobutylmethoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid (62.7 mg, 0.2 mmol) in N,N-dimethylformamide (1 mL) and the reaction mixture was left to stand for 20 minutes. 3-methyl butylamine (34.9 mg, 0.4 mmol) and N-ethyldiisopropylamine (103.4 mg, 0.8 mmol) were added and the reaction mixture was shaken for 16 hours. The solvent was removed in vacuo and the crude product was purified by preparative HPLC to afford 6-cyclobutylmethoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid (3-methyl-butyl)-amide as a solid 35.8 mg (52% yield) LC@215 nm; Rt 2.63: 100%, m/z (ES+): 347 (M+H).
Workup
- waitthe reaction mixture was left
- customThe solvent was removed in vacuo
- customthe crude product was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-0b91acc27412457f8a247eeb892ad9c9
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691863B2
Reaction notes
Loading…