Hydrochloric Acid → HCID 57461323, compound

HRID 1629204Notes

Reaction equation

HRID 1629204 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[N:10]1[C:14]([N:15]2[N:24]=[C:23]3[C:17]([CH2:18][CH2:19][O:20][C:21]4[CH:28]=[CH:27][C:26]([CH:29]5[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]5)=[CH:25][C:22]=43)=[CH:16]2)=[N:13][CH:12]=[N:11]1.Br[CH2:36][C:37]([NH2:39])=[O:38].C(OCC)(=O)C.Cl>C1CCCCC1.C(Cl)Cl.O1CCOCC1.C(OCC)C>[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[N:10]1[C:14]([N:15]2[N:24]=[C:23]3[C:17]([CH2:18][CH2:19][O:20][C:21]4[CH:28]=[CH:27][C:26]([CH:29]5[CH2:34][CH2:33][N:32]([CH2:36][C:37]([NH2:39])=[O:38])[CH2:31][CH2:30]5)=[CH:25][C:22]=43)=[CH:16]2)=[N:13][CH:12]=[N:11]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 696322-BromoacetamideHCID 67050669HCID 67050669, compound

Product 1

HCID 57461323HCID 57461323, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Following the procedure for 143, 2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-9-piperidin-4-yl-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene hydrochloride was reacted with bromo acetamide. The crude product was subjected flash chromatography (SiO2, gradient 50 to 100% ethyl acetate in cyclohexane). Pure fractions were combined and concentrated diethyl ether. The resultant precipitate in vacuo and the resultant residue dissolved in DCM and treated with 4M HCl in dioxane then was collected by filtration to give 178 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.86 (s, 1 H); 8.48-8.43 (m, 1 H); 8.30 (s, 1 H); 8.05 (s, 1 H); 7.85 (td, J=8.75, 5.93 Hz, 1 H); 7.74-7.63 (m, 2 H); 7.41-7.34 (m, 1 H); 7.22 (d, J=2.30 Hz, 1 H); 7.10 (dd, J=8.45, 2.35 Hz, 1 H); 6.97 (d, J=8.39 Hz, 1 H); 4.22 (t, J=5.00 Hz, 2 H); 3.98 (d, J=4.37 Hz, 2 H); 3.60 (t, J=12.26 Hz, 2 H); 3.24-3.13 (m, 2 H); 3.06 (t, J=4.95 Hz, 2 H); 2.69-2.61 (m, 1 H); 1.87 (s, 4 H). LCMS: RT=7.46 min, M+H+=506

Workup

  1. filtrationthen was collected by filtration

Sources & evidence

ORD record
ord-1350d6a2fb364d2c9b5e04675871b677
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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