Pyrrolidine → 6-(1-{6-[3-Fluoro-4-(1-methyl-2-oxo-2-pyrrolidin-1-ylethoxy)phenyl]imidazo[1,2-a]pyrimidin-3-yl}cyclopropyl)quinoline

HRID 500154Notes

Reaction equation

HRID 500154 reaction equation
[F:1][C:2]1[CH:13]=[C:12]([C:14]2[CH:15]=[N:16][C:17]3[N:18]([C:20]([C:23]4([C:26]5[CH:27]=[C:28]6[C:33](=[CH:34][CH:35]=5)[N:32]=[CH:31][CH:30]=[CH:29]6)[CH2:25][CH2:24]4)=[CH:21][N:22]=3)[CH:19]=2)[CH:11]=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6]([OH:8])=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=[CH:49][CH:50]=[CH:51][C:46]=2[N:45]=N1.N1CCCC1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[F:1][C:2]1[CH:13]=[C:12]([C:14]2[CH:15]=[N:16][C:17]3[N:18]([C:20]([C:23]4([C:26]5[CH:27]=[C:28]6[C:33](=[CH:34][CH:35]=5)[N:32]=[CH:31][CH:30]=[CH:29]6)[CH2:25][CH2:24]4)=[CH:21][N:22]=3)[CH:19]=2)[CH:11]=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6](=[O:8])[N:45]1[CH2:46][CH2:51][CH2:50][CH2:49]1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 672248532-[2-Fluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]phenoxy]propanoic acid

Product 1

HCID 251436916-(1-{6-[3-Fluoro-4-(1-methyl-2-oxo-2-pyrrolidin-1-ylethoxy)phenyl]imidazo[1,2-a]pyrimidin-3-yl}cyclopropyl)quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{2-fluoro-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]phenoxy}propanoic acid (59.1 mg, 0.126 mmol) in N,N-dimethylformamide (1.0 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (56 mg, 0.126 mmol), pyrrolidine (9.0 mg, 0.13 mmol) and N,N-diisopropylethylamine (0.1 mL) at RT. The mixture was stirred at RT for 3 h, and then purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=522.0.

Workup

  1. custompurified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-d02d454560384bc3a11b77c08fc88245
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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