1-Isopropylhydrazine → 9-chloro-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine

HRID 1530519Notes

Reaction equation

HRID 1530519 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][N:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16](/[N:18]=[CH:19]/[N:20](C)C)=O)[N:11]=1)[CH2:7][CH2:6][O:5]2.[CH:23]([NH:26]N)([CH3:25])[CH3:24]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][N:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:26]([CH:23]([CH3:25])[CH3:24])[N:20]=[CH:19][N:18]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2

Participants

4

Reactant 2

HCID 527891-IsopropylhydrazineHCID 178484342HCID 178484342, compound

Product 1

HCID 582045209-chloro-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepineYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 12-chloro-N-[(1E)-(dimethylamino)methylidene]-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene-4-carboxamide (0.25 mmol, 80 mg) in acetic acid (3 mL) was added hydrochloric isopropylhydrazine (0.50 mmol, 5 mg). The mixture was stirred at 100° C. for 1 h under nitrogen atmosphere. After removal of the solvent, the residue was purified by reverse phase combiflash eluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3 to give 12-chloro-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (50 mg, 61% yield). LCMS (ESI) m/z: 331.1 [M+H+]. 1H NMR (500 MHz, DMSO-d6): δ 9.29 (s, 1H), 8.02 (s, 1H), 7.94 (s, 1H), 7.24 (s, 1H), 5.86 (t, J=13.5 Hz, 1H), 4.68-4.65 (m, 2H), 4.61-4.59 (m, 2H), 1.49 (d, J=6.5 Hz, 6H)

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by reverse phase combiflash
  3. washeluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record
ord-e81bcac9de394f71b52b58243825e0ab
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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