2-Iodobenzoic acid → 12-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene-13-carbaldehyde

HRID 1530581Notes

Reaction equation

HRID 1530581 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[CH2:16][OH:17])[C:12]1[N:8]([CH:9]=[C:10]([C:18]3[N:22]([CH:23]([CH3:25])[CH3:24])[N:21]=[CH:20][N:19]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.IC1C=CC=CC=1C(O)=O>CCOC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[CH:16]=[O:17])[C:12]1[N:8]([CH:9]=[C:10]([C:18]3[N:22]([CH:23]([CH3:25])[CH3:24])[N:21]=[CH:20][N:19]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2

Participants

4

Reactant 2

HCID 69412-Iodobenzoic acidHCID 68312830HCID 68312830, compound

Product 1

HCID 8667146812-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene-13-carbaldehydeYield 71.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of {12-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}methanol (92 mg, 0.271 mmol) in EtOAc (10 mL) was added 2-iodobenzoic acid (304 mg, 1.086 mmol). The mixture was heated at 80° C. overnight. The solid was filtered, the filtrate was concentrated and purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:1) to give 12-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene-13-carbaldehyde (65 mg, 71% yield) as a yellow solid. LCMS (ESI) m/z: 338.1 [M+H+].

Workup

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified by silica gel chromatography
  4. washeluting with EtOAc/petroleum ether (1:1)

Sources & evidence

ORD record
ord-5a512befcf084eaa8065ed8ccecb5520
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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