3-Carboxybenzaldehyde → HCID 87208794, compound

HRID 1958813Notes

Reaction equation

HRID 1958813 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)=[O:2].C1C=CC2N(O)N=NC=2C=1.[OH:22][CH2:23][C:24]([NH:26][CH2:27][CH:28]([OH:43])[CH2:29][O:30][C:31]1[C:36]([CH3:37])=[CH:35][C:34]([C:38](=[NH:41])[NH:39]O)=[CH:33][C:32]=1[CH3:42])=[O:25].CCN=C=NCCCN(C)C.Cl>C1COCC1.CN(C=O)C>[CH:1]([C:3]1[CH:4]=[C:5]([C:6]2[O:8][N:41]=[C:38]([C:34]3[CH:33]=[C:32]([CH3:42])[C:31]([O:30][CH2:29][CH:28]([OH:43])[CH2:27][NH:26][C:24](=[O:25])[CH2:23][OH:22])=[C:36]([CH3:37])[CH:35]=3)[N:39]=2)[CH:9]=[CH:10][CH:11]=1)=[O:2]

Participants

7

Reactant 4

HCID 120773-CarboxybenzaldehydeHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178426660HCID 178426660, compound

Product 1

HCID 87208794HCID 87208794, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-formyl-benzoic acid (170 mg, 1.13 mmol), HOBt (184 mg, 1.36 mmol) and rac-2-hydroxy-N-{2-hydroxy-3-[4-(N-hydroxycarbamimidoyl)-2,6-dimethyl-phenoxy]-propyl}-acetamide (352 mg, 1.13 mmol) in THF (4 mL) and DMF (6 mL) was cooled to 0° C. before EDC hydrochloride (239 mg, 1.24 mmol) was added in portions. The mixture was stirred at rt for 1 h before it was diluted with THF (4 mL) and heated to 80° C. for 16 h. The mixture was concentrated and then separated by prep. HPLC (Waters XBridge Prep C18, 75×30 mm ID, 5 μm, 90% to 10% water (containing 0.5% of formic acid) in MeCN) to give the title compound as a white solid (130 mg). LC-MS*: tR=0.75 min; [M+1]+=425.90, 1H NMR (D6-DMSO): δ 2.35 (s, 6H), 3.20-3.29 (m, 1H), 3.40-3.49 (m, 1H), 3.71-3.82 (m, 2H), 3.84 (d, J=5.0 Hz, 2H), 3.92-4.00 (m, 1H), 5.30 (d, J=4.8 Hz, 1H), 5.55 (t, J=5.5 Hz, 1H), 7.70 (br t, J=4.8 Hz, 1H), 7.81 (s, 2H), 7.91 (t, J=7.8 Hz, 1H), 8.24 (d, J=7.5 Hz, 1H), 8.49 (d, J=7.8 Hz, 1H), 8.69 (s, 1H), 10.18 (s, 1H).

Workup

  1. additionwas added in portions
  2. temperatureheated to 80° C. for 16 h
  3. concentrationThe mixture was concentrated
  4. customseparated by prep

Sources & evidence

ORD record
ord-136c64581e7d4897bf554f65e65c7803
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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