Tetrahydrofuran → HCID 178523791, compound

HRID 2089061Notes

Reaction equation

HRID 2089061 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[N:5]=[C:4]([NH:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]2)[N:3]=1.[CH:25]1([C:28](Cl)=[O:29])CC1.CCN(C(C)C)C(C)C.[CH2:40]1[CH2:44][O:43][CH2:42][CH2:41]1>O>[C:28]([O-:29])(=[O:43])[CH3:25].[NH4+:3].[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[N:5]=[C:4]([NH:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([NH:24][C:42]([CH:41]3[CH2:40][CH2:44]3)=[O:43])[CH2:20][CH2:19]2)[N:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 178511662HCID 178511662, compound

Product 2

HCID 517165Ammonium AcetateHCID 178523791HCID 178523791, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 42c (120 mg, 0.35 mmol), cyclopropanecarbonyl chloride (36.6 mg, 0.35 mmol), and Hunig's base (0.18 mL, 1.05 mmol) in THF (2.5 mL) was stirred at room temperature for 16 hours. The reaction mixture was concentrated and purified by reverse-phase HPLC performed on a Phenomenex Luna C8 AXIA column (30×75 mm, 100 Å) using a gradient of 10% to 95% acetonitrile: 10 mM ammonium acetate in water over 12 minutes at a flow rate of 50 mL/minutes to provide title compound (20 mg, 0.049 mmol, 14% yield). MS (ESI) m/e 411 (M+H)+; 1H NMR (400 MHz, DMSO-d6) ppm 0.56-0.64 (m, 2H) 0.65-0.72 (m, 2H) 1.30-1.47 (m, 4H) 1.49-1.59 (m, 1H) 1.84-1.95 (m, J=6.41 Hz, 2H) 2.00-2.10 (m, 2H) 3.51-3.66 (m, 1H) 3.73-3.86 (m, J=7.63 Hz, 1H) 7.03 (d, J=7.63 Hz, 1H) 7.08 (s, 1H) 7.18 (dd, J=7.93, 4.58 Hz, 1H) 7.54-7.64 (m, 1H) 8.27-8.31 (m, 1H) 8.34 (s, 1H) 8.79 (d, J=7.63 Hz, 1H) 12.00 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-a2ff71d6bb984002a38ced7be58c3e45
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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