2-Iodobenzoic acid → HCID 86671463, compound

HRID 1530531Notes

Reaction equation

HRID 1530531 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][N:14]=[C:15]([N:23]3[CH2:27][CH2:26][CH2:25][CH:24]3[CH2:28][OH:29])[CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:3].IC1C=CC=CC=1C(O)=O>C(OCC)(=O)C>[CH3:3][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][N:14]=[C:15]([N:23]3[CH2:27][CH2:26][CH2:25][CH:24]3[CH:28]=[O:29])[CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:1]

Participants

4

Reactant 2

HCID 69412-Iodobenzoic acidHCID 68313050HCID 68313050, compound

Product 1

HCID 86671463HCID 86671463, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (1-{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-pentaen-12-yl}pyrrolidin-2-yl)methanol (173 mg, 0.436 mmol), 2-iodobenzoic acid (305 mg, 1.09 mmol) in ethyl acetate (10.0 mL) was refluxed for 6 hr. After filtration, the filtrated was evaporated to afford 1-{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-pentaen-12-yl}pyrrolidine-2-carbaldehyde (160 mg, 92% yield) as pale yellow solid. LCMS (ESI) m/z: 394.3 [M+H+].

Workup

  1. temperaturewas refluxed for 6 hr
  2. filtrationAfter filtration
  3. customthe filtrated was evaporated

Sources & evidence

ORD record
ord-1e5783d11abd41128d3240c3307a1197
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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