Trifluoroacetic acid → 4-(6-Chloro-8-morpholino-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)-2-fluorobenzoic acid trifluoroacetic acid salt

HRID 718709Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[C:5]2[N:6]([C:8]([C:24]3[CH:36]=[CH:35][C:27]([C:28]([O:30]C(C)(C)C)=[O:29])=[C:26]([F:37])[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:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>>[F:47][C:46]([F:49])([F:48])[C:44]([OH:50])=[O:45].[Cl:1][C:2]1[CH:3]=[C:4]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[C:5]2[N:6]([C:8]([C:24]3[CH:36]=[CH:35][C:27]([C:28]([OH:30])=[O:29])=[C:26]([F:37])[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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 117728451tert-butyl 4-(6-chloro-8-morpholino-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)-2-fluorobenzoate

Product 1

HCID 1177283464-(6-Chloro-8-morpholino-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)-2-fluorobenzoic acid trifluoroacetic acid salt

Procedure

Compound 81a (30 mg, 0.05 mmol) was treated with TFA using the procedures previously described in Example 80 to afford the title compound 165. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.87 (d, J=8.6 Hz, 1H), 8.20 (d, J=8.6 Hz, 1H), 8.02-8.12 (m, 2H), 7.99 (t, J=8.1 Hz, 1H), 7.84 (t, J=7.1 Hz, 1H), 7.71 (d, J=9.1 Hz, 1H), 7.58-7.66 (m, 2H), 6.46 (s, 1H), 4.05-4.14 (m, 4H), 3.85-3.95 (m, 4H), 3.18-3.25 (m, 1H), 3.08-3.16 (m, 1H), 2.22-2.30 (m, 1H), 2.16 (m, 1H); Mass Spectrum (LCMS, ESI pos.): Calcd. for C29H24ClN5O3: 526.1 (M+H). found: 526.3.

Sources & evidence

ORD record: ord-7863e67185e94b3d8dd203be73854d36
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

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