Benzoyl chloride → HCID 25226761, compound

HRID 1514373Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][C@@H:9]1[CH2:14][NH:13][CH2:12][CH2:11][N:10]1[C:15]1[N:16]=[N:17][C:18]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=12.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:8][C@H:9]1[N:10]([C:15]2[N:16]=[N:17][C:18]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=3)=[C:19]3[CH:24]=[CH:23][N:22]=[CH:21][C:20]=23)[CH2:11][CH2:12][N:13]([C:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:42])[CH2:14]1

Participants

Conditions

Temperature: 25 °C

Procedure

To triethylamine (0.315 ml, 2.26 mmol) and (R)-4-(2-methylpiperazin-1-yl)-1-(4-(trifluoromethyl)phenyl)pyrido[3,4-d]pyridazine 21 (0.352 g, 0.943 mmol), in CH2Cl2 (3.1 ml) was added benzoyl chloride (0.120 ml, 1.04 mmol). The reaction was stirred at 25° C. After 2 h, the reaction contents were poured into saturated sodium bicarbonate (10 mL) and extracted with dichloromethane (3×15 mL). The combined organics were dried with Na2SO4 and concentrated in vacuo. Silica gel chromatography (gradient elution 20 to 90% EtOAc in CH2Cl2) afforded 347 mg of desired product (R)-(3-methyl-4-(1-(4-(trifluoromethyl)phenyl)pyrido[3,4-d]pyridazin-4-yl)piperazin-1-yl)(phenyl)methanone 22 (77% yield). 1H NMR (500 MHz, CDCl3) δ ppm 9.57 (s, 1H) 8.96 (d, J=6.1 Hz, 1H) 7.81-7.97 (m, 4H) 7.77 (d, J=5.5 Hz, 1H) 7.47 (s, 5H) 3.30-4.82 (m, 7H) 1.29-1.53 (m, 3H).

Workup

customthe reaction contents
extractionextracted with dichloromethane (3×15 mL)
dry with materialThe combined organics were dried with Na2SO4
concentrationconcentrated in vacuo
washSilica gel chromatography (gradient elution 20 to 90% EtOAc in CH2Cl2)

Sources & evidence

ORD record: ord-8cb099b06ed84fc49a40434e5d36e16a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222251B2

Reaction notes

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