PyBroP → HCID 68351888, compound

HRID 68885Notes

Reaction equation

HRID 68885 reaction equation
F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[CH:25]1([NH:28][CH:29]2[CH2:34][CH2:33][N:32]([C:35]3[C:40]([F:41])=[CH:39][C:38]([C:42]([F:45])([F:44])[F:43])=[CH:37][N:36]=3)[CH2:31][CH2:30]2)[CH2:27][CH2:26]1.[CH3:46][C:47]1[N:48]([C:52]2[CH:60]=[CH:59][C:55]([C:56](O)=[O:57])=[CH:54][CH:53]=2)[CH:49]=[CH:50][N:51]=1.C(#N)C.O.FC(F)(F)C(O)=O>CN(C)C=O.C(N(CC)CC)C>[CH:25]1([N:28]([CH:29]2[CH2:34][CH2:33][N:32]([C:35]3[C:40]([F:41])=[CH:39][C:38]([C:42]([F:44])([F:43])[F:45])=[CH:37][N:36]=3)[CH2:31][CH2:30]2)[C:56](=[O:57])[C:55]2[CH:54]=[CH:53][C:52]([N:48]3[CH:49]=[CH:50][N:51]=[C:47]3[CH3:46])=[CH:60][CH:59]=2)[CH2:26][CH2:27]1

Participants

7

Reactant 4

HCID 2733179PyBroPHCID 138159884-(2-methyl-1H-imidazol-1-yl)benzoic acidHCID 22145617Water TFA acetonitrileHCID 68289864Cyclopropyl-(3'-fluoro-5'-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-amine

Product 1

HCID 68351888HCID 68351888, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP, 14 mg) in N,N-dimethylformamide (0.1 mL) is added to a solution of cyclopropyl-(3′-fluoro-5′-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-amine (6 mg), 4-(2-methyl-imidazol-1-yl)-benzoic acid (6 mg), and triethylamine (0.015 mL) in N,N-dimethylformamide (0.4 mL) at room temperature. The solution is stirred for 2 h and then submitted to chromatography on reversed phase (HPLC, acetonitrile/water/trifluoroacetic acid) to give the pure title compound. LC (method 19): tR=4.33 min; Mass spectrum (ESI+): m/z=488 [M+H]+.

Sources & evidence

ORD record
ord-5fe8b229671444bd85125f8101e0a23e
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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