Diisopropylethylamine → HCID 67211256, compound

HRID 1892552Notes

Reaction equation

HRID 1892552 reaction equation
[F:1][C:2]1[C:7]2[C:8]([C:18](O)=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:21].C1C=[C:26]2[N:28]=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.Cl.C(N(CC)C(C)C)(C)C>>[F:1][C:2]1[C:7]2[C:8]([C:18]([NH:28][CH3:26])=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:21]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67211105HCID 67211105, compound

Product 1

HCID 67211256HCID 67211256, compound

Procedure

To a mixture of 4-fluoro-2-(4-fluorophenyl)-5-hydroxybenzofuran-3-carboxylic acid (73 mg, 0.252 mmol), methylamine, HCl (25.5 mg, 0.377 mmol), HOBT hydrate (65.5 mg, 0.428 mmol) and EDC hydrochloride (87 mg, 0.453 mmol) at r.t. under N2 was added N,N-diisopropylethylamine (0.220 mL, 1.258 mmol). The mixture was stirred at r.t. for 16 hours. After concentration, the mixture was added with 5 ml 1N HCl, and then 14 ml H2O. The white solid was filtered and washed with 3×5 ml H2O and dried (64 mg). 1H NMR (500 MHz, CD3OD) δ 7.89 (dd, J=8.09, 5.34, 2H), 7.25 (t overlapping with dd, 2H), 7.23 (dd, 1H), 6.99 (t, J=8.55, 1H), 2.96 (s, 3H). LC/MS were performed by using Shimadzu-VP instrument with UV detection at 220 nm and Waters Micromass. HPLC method: Solvent A=10% MeOH—90% H2O—0.1% TFA, Solvent B=90% MeOH—10% H2O—0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Stop time=3 min, Flow Rate=5 ml/min, Column: Phenomenex-Luna, 3.0×50 mm, S10; (ES+) m/z (M+H)+=304.06, HPLC Rt=1.262 min.

Workup

  1. concentrationAfter concentration
  2. additionthe mixture was added with 5 ml 1N HCl
  3. filtrationThe white solid was filtered
  4. washwashed with 3×5 ml H2O
  5. customdried (64 mg)
  6. customB=100, Gradient time=2 min
  7. customtime=3 min, Flow Rate=5 ml/min, Column

Sources & evidence

ORD record
ord-e68b9113082844cabc2adf2f760f43e0
Source dataset
uspto-grants-2013_08
Patent number
US08507683B2

Reaction notes

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