Diisopropylethylamine → HCID 123960931, compound

HRID 535550Notes

Reaction equation

HRID 535550 reaction equation
[NH2:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]([NH:14][C:15](=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:4]=1.CCN(C(C)C)C(C)C.[C:34](Cl)(=[O:42])[O:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C(Cl)Cl.CCOCC>[CH:36]1([O:35][C:34](=[O:42])[NH:1][CH2:2][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:13])[N:5]([NH:14][C:15](=[O:24])[CH2:16][C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:4]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 83262Carbonochloridic acid, cyclohexyl esterHCID 70976268HCID 70976268, compound

Product 1

HCID 123960931HCID 123960931, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of Example 42 (90 mg, 0.26 mmol), iPr2NEt (0.078 mL, 0.45 mmol), and cyclohexyl carbonochloridate (51.2 mg, 0.315 mmol) in DCM (4 mL) was stirred at room temperature for 8 hours, diluted with Et2O, washed with sat NaHCO3 and brine, dried (MgSO4), filtered, concentrated, and chromatographed (17-25% EtOAc/DCM) to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.60 (s, 1H), 8.32 (dd, J=7.8, 1.4 Hz, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.97-8.03 (m, 1H), 7.91 (td, J=7.5, 1.2 Hz, 1H), 7.60-7.65 (m, 1H), 7.41 (s, 4H), 4.47-4.51 (m, 3H), 3.67 (s, 2H), 1.58-1.84 (m, 4H), 1.41-1.54 (m, 1H), 1.10-1.35 (m, 4H); MS (ESI−) M/Z 467 (M−H)−.

Workup

  1. washwashed
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (17-25% EtOAc/DCM)

Sources & evidence

ORD record
ord-eba5a92365184361befacbb0f49f4848
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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