Triethylamine → HCID 67980090, compound

HRID 407066Notes

Reaction equation

HRID 407066 reaction equation
[C:1](=O)([O:7]C1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][CH:4]1[CH2:6][CH2:5]1.[C:18]([CH2:20][C:21]1([N:25]2[CH:29]=[C:28]([C:30]3[CH:35]=[N:34][N:33]4[C:36]([C:39]5[CH:40]=[C:41]([NH:45][C:46]([NH:48][CH2:49][C:50]([F:53])([F:52])[F:51])=[O:47])[CH:42]=[CH:43][CH:44]=5)=[CH:37][N:38]=[C:32]4[CH:31]=3)[CH:27]=[N:26]2)[CH2:24][NH:23][CH2:22]1)#[N:19].C(N(CC)CC)C>CN(C)C=O.CO>[C:18]([CH2:20][C:21]1([N:25]2[CH:29]=[C:28]([C:30]3[CH:35]=[N:34][N:33]4[C:36]([C:39]5[CH:44]=[CH:43][CH:42]=[C:41]([NH:45][C:46]([NH:48][CH2:49][C:50]([F:52])([F:53])[F:51])=[O:47])[CH:40]=5)=[CH:37][N:38]=[C:32]4[CH:31]=3)[CH:27]=[N:26]2)[CH2:22][N:23]([C:1]([O:2][CH2:3][CH:4]2[CH2:6][CH2:5]2)=[O:7])[CH2:24]1)#[N:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11183976HCID 11183976, compoundHCID 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 67980090HCID 67980090, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Cyclopropylmethyl 4-nitrophenyl carbonate (11 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=594.2.

Workup

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

Sources & evidence

ORD record
ord-af3e2e5a58314be9b2190974dcf7b5b3
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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