Sodium Methoxide → 2-(4-(6-Chloro-8-morpholino-2-((1R,25)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)phenyl)acetate sodium salt

HRID 718711Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[C:5]2[N:6]([C:8]([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:33]C)=[O:32])=[CH:26][CH:25]=3)=[C:9]([C@@H:11]3[CH2:13][C@@H:12]3[C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[N:10]=2)[N:7]=1.C[O-].[Na+:43]>>[Na+:43].[Cl:1][C:2]1[CH:3]=[C:4]([N:35]2[CH2:36][CH2:37][O:38][CH2:39][CH2:40]2)[C:5]2[N:6]([C:8]([C:24]3[CH:25]=[CH:26][C:27]([CH2:30][C:31]([O-:33])=[O:32])=[CH:28][CH:29]=3)=[C:9]([C@@H:11]3[CH2:13][C@@H:12]3[C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[N:10]=2)[N:7]=1

Participants

Reactant 2

HCID 10942334Sodium Methoxide

HCID 131734184Methyl 2-(4-(6-chloro-8-morpholino-2-((1R,25)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)phenyl)acetate

Product 1

HCID 1177283592-(4-(6-Chloro-8-morpholino-2-((1R,25)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)phenyl)acetate sodium salt

Procedure

Compound 82a (30 mg, 0.054 mmol) was treated with NaOMe (36 μL, 0.10 mmol) using the procedures described in Example 73, Step H to afford title compound 173. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.18 (d, J=8.6 Hz, 1H), 7.92 (d, J=8.1 Hz, 1H), 7.84 (d, J=8.1 Hz, 1H), 7.68 (t, J=7.6 Hz, 1H), 7.56 (d, J=8.1 Hz, 2H), 7.49 (t, J=6.8 Hz, 1H), 7.36 (d, J=8.6 Hz, 2H), 7.32 (d, J=8.6 Hz, 1H), 6.34 (s, 1H), 4.02-4.11 (m, 4H), 3.85-3.95 (m, 4H), 3.49 (s, 2H), 2.79-2.89 (m, 1H), 2.68-2.79 (m, 1H), 1.84-1.94 (m, 2H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C30H26ClN5O3: 540.1 (M+H). found: 539.8.

Sources & evidence

ORD record: ord-62c6313342894a7798fe4c972955150e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

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