Triethylamine → N-cyclopropyl-2-[4-[3-[3-(2,2,2-trifluoroethylcarbamoylamino)phenyl]imidazo[1,2-b]pyridazin-7-yl]pyrazol-1-yl]propanamide

HRID 407028

Reaction equation

HRID 407028 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[F:5][C:6]([F:38])([F:37])[CH2:7][NH:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([C:18]2[N:22]3[N:23]=[CH:24][C:25]([C:27]4[CH:28]=[N:29][N:30]([CH:32]([CH3:36])[C:33](O)=[O:34])[CH:31]=4)=[CH:26][C:21]3=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[CH:1]1([NH:4][C:33](=[O:34])[CH:32]([N:30]2[CH:31]=[C:27]([C:25]3[CH:24]=[N:23][N:22]4[C:18]([C:14]5[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][C:9]([NH:8][CH2:7][C:6]([F:38])([F:37])[F:5])=[O:10])[CH:13]=5)=[CH:19][N:20]=[C:21]4[CH:26]=3)[CH:28]=[N:29]2)[CH3:36])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 679802202-(4-{3-[3-({[(2,2,2-trifluoroethyl)amino]carbonyl}amino)phenyl]imidazo[1,2-b]pyridazin-7-yl}-1H-pyrazol-1-yl)propanoic acid

Product 1

HCID 57384630N-cyclopropyl-2-[4-[3-[3-(2,2,2-trifluoroethylcarbamoylamino)phenyl]imidazo[1,2-b]pyridazin-7-yl]pyrazol-1-yl]propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopropylamine (17 μL, 0.24 mmol) was added to a mixture of 2-(4-{3-[3-({[(2,2,2-trifluoroethyl)amino]carbonyl}amino)phenyl]imidazo[1,2-b]pyridazin-7-yl}-1H-pyrazol-1-yl)propanoic acid (0.16 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (110 mg, 0.24 mmol) in DMF (2.0 mL), followed by triethylamine (45 μL, 0.32 mmol). The reaction mixture was stirred at r.t. for 30 min. The mixture was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=513.2.

Workup

  1. customThe mixture was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-604fed29900f4f8ab83f2e9b565db997
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Linked notes

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