Diisopropylethylamine → HCID 66953826, compound

HRID 1424633Notes

Reaction equation

HRID 1424633 reaction equation
[CH2:1]([CH:4]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[O:5]1)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.[CH:28]12[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH:29]1[N:38]=[C:39]=[O:40])[CH2:35]2>C(Cl)Cl>[CH:30]12[CH2:36][CH:34]3[CH2:33][CH:32]([CH2:37][CH:28]([CH2:35]3)[CH:29]1[NH:38][C:39]([N:9]1[CH2:10][CH2:11][C:6]3([C:12]4[C:17](=[CH:16][CH:15]=[CH:14][C:13]=4[Cl:18])[CH:4]([CH2:1][CH:2]=[CH2:3])[O:5]3)[CH2:7][CH2:8]1)=[O:40])[CH2:31]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 128826302-IsocyanatoadamantaneHCID 58137314HCID 58137314, compound

Product 1

HCID 66953826HCID 66953826, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-allyl-7-chloro-3H-spiro[isobenzofuran-1,4′-piperidine] (0.0190 g), and DIEA (0.5 mL) in CH2Cl2 (2 mL) was added 2-adamantyl isocyanate (0.0138 g, 0.0778 mmol) at rt. After 19 h, the solvents were removed in vacuo and the residue was purified by reversed-phase HPLC (Phenomenex® Luna 5μ C18(2) 100A, 250×21.20 mm, 5 micron, 70%→90% CH3CN/H2O, 0.1% CF3COOH over 8 min and then 90% CH3CN/H2O, 0.1% CF3COOH over 4 min, flow rate 25 mL/min) to afford N-(2-adamantyl)-3-allyl-7-chloro-3H-spiro[isobenzofuran-1,4′-piperidine]-1′-carboxamide (0.0220 g, 97%). LC-MS Method 1 tR=2.33 min, m/z 443, 441 (MH+); 1H NMR (400 MHz, CDCl3) δ=7.24-7.20 (m, 2H), 7.09-7.05 (m, 1H), 5.87-5.77 (m, 1H), 5.25 (t, J=5.7 Hz, 1H), 5.15-5.08 (m, 2H), 3.98 (br s, 1H), 3.94-3.88 (m, 2H), 136-3.28 (m, 2H), 2.66-2.38 (m, 4H), 1.95-1.25 (m, 16H).

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue was purified by reversed-phase HPLC (Phenomenex® Luna 5μ C18(2) 100A, 250×21.20 mm, 5 micron, 70%
  3. customover 8 min
  4. wait90% CH3CN/H2O, 0.1% CF3COOH over 4 min

Sources & evidence

ORD record
ord-c69249f512284d6a98ac4024f123ccba
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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