Triethylamine → HCID 57386423, compound

HRID 407062Notes

Reaction equation

HRID 407062 reaction equation
[N:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:10]([CH2:12][C:13]1([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[N:26][N:25]4[C:28]([C:31]5[CH:32]=[C:33]([NH:37][C:38]([NH:40][CH2:41][C:42]([F:45])([F:44])[F:43])=[O:39])[CH:34]=[CH:35][CH:36]=5)=[CH:29][N:30]=[C:24]4[CH:23]=3)[CH:19]=[N:18]2)[CH2:16][NH:15][CH2:14]1)#[N:11].C(N(CC)CC)C>CN(C)C=O.CO>[C:10]([CH2:12][C:13]1([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[N:26][N:25]4[C:28]([C:31]5[CH:32]=[C:33]([NH:37][C:38]([NH:40][CH2:41][C:42]([F:44])([F:45])[F:43])=[O:39])[CH:34]=[CH:35][CH:36]=5)=[CH:29][N:30]=[C:24]4[CH:23]=3)[CH:19]=[N:18]2)[CH2:14][N:15]([C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:8])[CH2:16]1)#[N:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 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 57386423HCID 57386423, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Morpholine-4-carbonyl chloride (6.8 mg, 0.045 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 (15.0 mg, 0.0303 mmol) and triethylamine (13 μL, 0.093 mmol) in N,N-dimethylformamide (0.5 mL) and methanol (0.1 mL). The reaction mixture was stirred at r.t. for 2 h. The mixture was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=609.2.

Workup

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

Sources & evidence

ORD record
ord-465ab992d6744bed9264e76e22379b4a
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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