Hydrochloric Acid → (E)-3-(4-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzamido)propanoic acid

HRID 718575Notes

Reaction equation

HRID 718575 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:42]=[CH:41][C:31]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39]C)=[O:38])=[O:33])=[CH:30][CH:29]=4)=[C:14](/[CH:16]=[CH: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.[Li+].[OH-].O.Cl>C1COCC1.CO>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:42]=[CH:41][C:31]([C:32]([NH:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:33])=[CH:30][CH:29]=4)=[C:14](/[CH:16]=[CH: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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 117732459(E)-Methyl 3-(4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzamido)propanoate

Product 1

HCID 117728518(E)-3-(4-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Compound 7a (0.20 g, 0.36 mmol) was suspended in THF/MeOH (4:1 v/v, 5 mL), and treated with 1 N LiOH solution (2.0 mL). The resulting mixture was stirred at rt for 3 h, and treated with water. The pH of the mixture was adjusted to ca. pH 5 using 1 N HCl solution. The resulting mixture was extracted with DCM (2×200 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue obtained was washed with MeOH, and dried under high vacuum to give the title compound 44 as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.14 (d, J=8.6 Hz, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.97-8.03 (m, 3H), 7.94 (d, J=15.6 Hz, 1H), 7.76-7.86 (m, 3H), 7.64-7.76 (m, 3H), 7.46-7.55 (m, 1H), 6.15 (d, J=5.6 Hz, 1H), 4.08 (d, J=3.4 Hz, 4H), 4.01 (d, J=3.4 Hz, 4H), 3.74 (t, J=5.9 Hz, 2H), 2.70 (t, J=5.9 Hz, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C31H28N6O4: 549.2 (M+H). Found 549.2.

Workup

  1. extractionThe resulting mixture was extracted with DCM (2×200 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue obtained
  7. washwas washed with MeOH
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-d6ac20058ea84fea9aacb46f20ebbce5
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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