Diethyl Ether → 1-(4-(8-Morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-b]pyridazin-3-yl)phenyl)-1,2-dihydro-1,2,4-triazol-3-one trifluoroacetic acid salt

HRID 718653Notes

Reaction equation

HRID 718653 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[CH:38]=[N:37][C:36](=[O:39])[N:35]5COCC[Si](C)(C)C)=[CH:30][CH:29]=4)=[C:14]([CH2:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.CCOCC.[C:53]([OH:59])([C:55]([F:58])([F:57])[F:56])=[O:54].C(Cl)Cl>>[F:56][C:55]([F:58])([F:57])[C:53]([OH:59])=[O:54].[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:29]=[CH:30][C:31]([N:34]5[CH:38]=[N:37][C:36](=[O:39])[NH:35]5)=[CH:32][CH:33]=4)=[C:14]([CH2:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 21863450Trifluoroacetic acid methylene chlorideHCID 1231449431-(4-(8-Morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-b]pyridazin-3-yl)phenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-1,2-dihydro-1,2,4-triazol-3-one

Product 1

HCID 1177282541-(4-(8-Morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-b]pyridazin-3-yl)phenyl)-1,2-dihydro-1,2,4-triazol-3-one trifluoroacetic acid salt

Procedure

A solution of compound 52e (45 mg, 0.070 mmol) in TFA:DCM (1:3 v/v, 5 mL) was stirred overnight at rt. The resulting mixture was concentrated under reduced pressure and the residue obtained was treated with Et2O (10 mL). The solids formed were collected by filtration and washed with Et2O (2×20 mL). The title compound 59 was obtained as a yellow solid. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 8.92 (d, J=8.4 Hz, 1H), 8.87 (s, 1H), 8.25 (d, J=8.4 Hz, 1H), 8.06-8.03 (m, 3H), 7.94-7.85 (m, 2H), 7.72 (d, J=8.4 Hz, 2H), 7.64 (d, J=8.4 Hz, 2H), 6.30 (d, J=5.7 Hz, 1H), 3.56-3.43 (m, 12H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C29H26N8O2: 519.2 (M+H). Found: 519.1.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. customThe solids formed
  4. filtrationwere collected by filtration
  5. washwashed with Et2O (2×20 mL)

Sources & evidence

ORD record
ord-1583ed5d6f244e2e96f18b0476e6c4c9
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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