Diisopropylethylamine → HCID 59275554, compound

HRID 1025126Notes

Reaction equation

HRID 1025126 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]3[CH:29]=[CH:28][C:27]([C:30]4[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=4)[C:33](O)=[O:34])=[CH:26][C:20]=3[C:21]=2[C:22](=[O:25])[NH:23][CH3:24])=[CH:13][CH:12]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CO>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]3[CH:29]=[CH:28][C:27]([C:30]4[CH:38]=[CH:37][CH:36]=[C:32]([C:33]([N:2]5[CH2:3][C:4]6[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=6)[CH2:1]5)=[O:34])[CH:31]=4)=[CH:26][C:20]=3[C:21]=2[C:22]([NH:23][CH3:24])=[O:25])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 422478IsoindolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592754243-[2-(4-Fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-5-yl]benzoic acid

Product 1

HCID 59275554HCID 59275554, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Isoindoline (20 μL, 0.18 mmol) was added to a stirred suspension of 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)benzoic acid (20 mg, 0.051 mmol), HATU (25 mg, 0.066 mmol), and DIPEA (50 μL, 0.29 mmol) in DMF (0.5 mL). The reaction was stirred at r.t. overnight. The reaction was then diluted with MeOH and an off-white ppt. formed. The ppt. was collected by filtration, triturated with MeOH, and air dried to afford the title compound (17 mg, 68% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 8.50 (q, J=4.58 Hz, 1 H) 7.99-8.05 (m, 2 H) 7.90-7.95 (m, 2 H) 7.85 (dt, J=6.10, 2.44 Hz, 1 H) 7.77-7.81 (m, 1 H) 7.73-7.77 (m, 1 H) 7.58-7.64 (m, 2 H) 7.36-7.45 (m, 3 H) 7.30-7.34 (m, 1 H) 7.29 (s, 2 H) 4.91 (s, 2 H) 4.84 (s, 2 H) 2.86 (d, J=4.88 Hz, 3 H). LC/MS was performed on a Shimadzu-VP instrument with UV detection at 220 nm and Waters Micromass. LC/MS method: solvent A=10% CH3CN/90% H2O/0.1% TFA, solvent B=90% CH3CN/10% H2O/0.1% TFA, start % B=0, final % B=100, gradient time=3 min, stop time=4 min, flow rate=4 ml/min, column: Sunfire C18 5 μm 4.6×50 mm; HPLC Rt=2.48 min, (ES+) m/z (MH+)=491. Analytical HPLC method: solvent A=5% CH3CN/95% H2O/0.1% TFA, solvent B=95% CH3CN/5% H2O/0.1% TFA, start % B=10, final % B=100, gradient time=15 min, stop time=18 min, flow rate=1 ml/min. Column: Waters Sunfire C-18, 3.5 μm 4.6×150 mm, Rt=13.81 min, purity=100%; column: Waters Xbridge Phenyl 3.5 μm 4.6×150 mm, Rt=13.81 min, purity=100%.

Workup

  1. customformed
  2. filtrationwas collected by filtration
  3. customtriturated with MeOH, and air
  4. customdried

Sources & evidence

ORD record
ord-e1465f8b6f45407aa77436c0a9e787f5
Source dataset
uspto-grants-2014_05
Patent number
US08722688B2

Reaction notes

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