Triethylamine → N-{3-[7-(1-{3-(cyanomethyl)-1-[(1-methyl-1H-pyrazol-3-yl)sulfonyl]azetidin-3-yl}-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]phenyl}-N'-(2,2,2-trifluoroethyl)urea

HRID 407050Notes

Reaction equation

HRID 407050 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[N:3]1.[C:11]([CH2:13][C:14]1([N:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[N:27][N:26]4[C:29]([C:32]5[CH:33]=[C:34]([NH:38][C:39]([NH:41][CH2:42][C:43]([F:46])([F:45])[F:44])=[O:40])[CH:35]=[CH:36][CH:37]=5)=[CH:30][N:31]=[C:25]4[CH:24]=3)[CH:20]=[N:19]2)[CH2:17][NH:16][CH2:15]1)#[N:12].C(N(CC)CC)C>C(#N)C.CO>[C:11]([CH2:13][C:14]1([N:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[N:27][N:26]4[C:29]([C:32]5[CH:33]=[C:34]([NH:38][C:39]([NH:41][CH2:42][C:43]([F:45])([F:46])[F:44])=[O:40])[CH:35]=[CH:36][CH:37]=5)=[CH:30][N:31]=[C:25]4[CH:24]=3)[CH:20]=[N:19]2)[CH2:15][N:16]([S:7]([C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)(=[O:9])=[O:8])[CH2:17]1)#[N:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 134744661-Methyl-1H-pyrazole-3-sulfonyl 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 57385637N-{3-[7-(1-{3-(cyanomethyl)-1-[(1-methyl-1H-pyrazol-3-yl)sulfonyl]azetidin-3-yl}-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]phenyl}-N'-(2,2,2-trifluoroethyl)urea

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

1-Methyl-1H-pyrazole-3-sulfonyl chloride (5.5 mg, 0.030 mmol) (Maybridge and Cat. No. CC 48303) 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 (10.0 mg, 0.0202 mmol) and triethylamine (8.4 μL, 0.060 mmol) in acetonitrile (1.0 mL) and MeOH (0.2 mL). 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=640.2.

Workup

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

Sources & evidence

ORD record
ord-959f0c09787347ea8b74bf0c22c1dcad
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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