Trifluoroacetic acid methylene chloride → 2-(5-(8-Morpholino-2-(2-(quinolin-2-yl)ethynyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-ylamino)acetic acid trifluoroacetic acid salt

HRID 718622Notes

Reaction equation

HRID 718622 reaction equation
C(OC([N:8]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:27]3[N:28]=[CH:29][CH:30]=[C:31]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[C:26]3=[N:25][C:24]=2[C:38]#[C:39][C:40]2[CH:49]=[CH:48][C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[N:41]=2)=[CH:19][N:18]=1)[CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])=O)(C)(C)C.[C:50]([OH:56])([C:52]([F:55])([F:54])[F:53])=[O:51].C(Cl)Cl>CCOCC>[F:53][C:52]([F:55])([F:54])[C:50]([OH:56])=[O:51].[O:35]1[CH2:36][CH2:37][N:32]([C:31]2[C:26]3[N:27]([C:23]([C:20]4[CH:21]=[CH:22][C:17]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[N:18][CH:19]=4)=[C:24]([C:38]#[C:39][C:40]4[CH:49]=[CH:48][C:47]5[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=5)[N:41]=4)[N:25]=3)[N:28]=[CH:29][CH:30]=2)[CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 117732492tert-Butyl 2-(tert-butoxycarbonyl(5-(8-morpholino-2-(quinolin-2-ylethynyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)amino)acetate

Product 1

HCID 1177284492-(5-(8-Morpholino-2-(2-(quinolin-2-yl)ethynyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-ylamino)acetic acid trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Compound 38b (0.40 g, 0.57 mmol) was treated with TFA:DCM (1:4 v/v, 15 mL) dropwise with stirring at 0° C. The resulting mixture was stirred for 30 min at rt and concentrated under reduced pressure. The residue obtained was treated with 10 mL of Et2O. The solids formed were collected by filtration and washed with Et2O (2×30 mL) to obtain the title compound 24 as an orange solid. 1H-NMR (300 MHz, DMSO-d6+D2O) δ (ppm): 8.64 (s, 1H), 8.42 (d, J=8.4 Hz, 1H), 8.35 (d, J=9.3 Hz, 1H), 8.21 (d, J=5.4 Hz, 1H), 8.01-7.99 (m, 2H), 7.82 (t, J=15.3 Hz, 1H), 7.70-7.63 (m, 2H), 7.10 (d, J=9.3 Hz, 1H), 6.43 (d, J=5.7 Hz, 1H), 4.16 (s, 2H), 4.02-3.94 (m, 4H), 3.82-3.70 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H23N2O3: 506.2 (M+H). Found: 506.1.

Workup

  1. stirringThe resulting mixture was stirred for 30 min at rt
  2. concentrationconcentrated under reduced pressure
  3. customThe residue obtained
  4. customThe solids formed
  5. filtrationwere collected by filtration
  6. washwashed with Et2O (2×30 mL)

Sources & evidence

ORD record
ord-f0678b07c22f4094be1e21a15c1ed42b
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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