Triethylamine → HCID 57385890, compound

HRID 407054Notes

Reaction equation

HRID 407054 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[C:7]([CH2:9][C:10]1([N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[N:23][N:22]4[C:25]([C:28]5[CH:29]=[C:30]([NH:34][C:35]([NH:37][CH2:38][C:39]([F:42])([F:41])[F:40])=[O:36])[CH:31]=[CH:32][CH:33]=5)=[CH:26][N:27]=[C:21]4[CH:20]=3)[CH:16]=[N:15]2)[CH2:13][NH:12][CH2:11]1)#[N:8].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)C=O>[C:1]([CH2:3][C:4]([N:12]1[CH2:13][C:10]([N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[N:23][N:22]4[C:25]([C:28]5[CH:29]=[C:30]([NH:34][C:35]([NH:37][CH2:38][C:39]([F:42])([F:41])[F:40])=[O:36])[CH:31]=[CH:32][CH:33]=5)=[CH:26][N:27]=[C:21]4[CH:20]=3)[CH:16]=[N:15]2)([CH2:9][C:7]#[N:8])[CH2:11]1)=[O:6])#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67980375N-[3-(7-{1-[3-(cyanomethyl)azetidin-3-yl]-1H-pyrazol-4-yl]imidazo[1,2-b]pyridazin-3-yl)phenyl]-N'-(2,2,2-trifluoroethyl)urea

Product 1

HCID 57385890HCID 57385890, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyanoacetic acid (3.1 mg, 0.036 mmol) was added to a mixture of N-[3-(7-{1-[3-(cyanomethyl)azetidin-3-yl]-1H-pyrazol-4-yl}imidazo[1,2-b]pyridazin-3-yl)phenyl]-N′-(2,2,2-trifluoroethyl)urea (11.9 mg, 0.0241 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (16 mg, 0.036 mmol) in N,N-dimethylformamide (0.6 mL), followed by triethylamine (10. μL, 0.072 mmol). The reaction mixture was stirred at r.t. for 1 h. The mixture was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=563.2.

Workup

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

Sources & evidence

ORD record
ord-3c97397f17bd4fe8b44ea778dd881419
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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