Tert-butyl 4-bromobenzoate → tert-Butyl 4-(6-chloro-8-morpholino-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)benzoate

HRID 718707Notes

Reaction equation

HRID 718707 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:5]2[N:6]([CH:8]=[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.Br[C:31]1[CH:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:33][CH:32]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:5]2[N:6]([C:8]([C:31]3[CH:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])=[CH:33][CH:32]=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

3

Reactant 2

HCID 11334366Tert-butyl 4-bromobenzoateHCID 1177284914-(6-Chloro-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-8-yl)morpholine

Product 1

HCID 131734183tert-Butyl 4-(6-chloro-8-morpholino-2-((1R,2S)-2-(quinolin-2-yl)cyclopropyl)imidazo[1,2-b]pyridazin-3-yl)benzoate

Procedure

Compound 79d (33 mg, 0.081 mmol) was coupled with tert-butyl 4-bromobenzoate (29 μL, 0.12 mmol) using the procedure described in Example 20, Step A to afford title compound 146. 1H NMR (400 MHz, CD3OD) δ (ppm): 7.93-8.08 (m, 4H), 7.72-7.85 (m, 3H), 7.66 (t, J=7.6 Hz, 1H), 7.41-7.50 (m, 1H), 7.24-7.31 (m, 1H), 6.12 (s, 1H), 4.05 (br. s., 4H), 3.95 (d, J=3.9 Hz, 4H), 2.80-2.93 (m, 2H), 1.87-2.00 (m, 2H), 1.58 (s, 9H) Mass Spectrum (LCMS, ESI pos.): Calcd. for C33H32ClN5O3: 582.2 (M+H). found: 582.2.

Sources & evidence

ORD record
ord-4988ef8e173e4b77a0f2c33d0097a30b
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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