Hydrochloric Acid → HCID 66953338, compound

HRID 1424598Notes

Reaction equation

HRID 1424598 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]3([C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][NH:21][CH2:20]3)[CH2:16][CH2:15]1)=[O:13])[CH2:8]2.CCN(C(C)C)C(C)C.[CH3:38][N:39]=[C:40]=[O:41].Cl>C(Cl)Cl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]3([C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][N:21]([C:40]([NH:39][CH3:38])=[O:41])[CH2:20]3)[CH2:16][CH2:15]1)=[O:13])[CH2:8]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 25064399N-(2-adamantyl)-2,3-dihydro-1H-spiro[isoquinoline-4,4'-piperidine]-1'-carboxamide

Product 1

HCID 66953338HCID 66953338, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vial was charged with N-(2-adamantyl)-2,3-dihydro-1H-spiro[isoquinoline-4,4′-piperidine]-1′-carboxamide (15 mg, 40 μmol), i-Pr2NEt (11 μL, 60 μmol) and CH2Cl2 (1 mL). Methyl isocyanate (3 μL, 43 μmol) was added and the mixture was stirred overnight at rt. A 10-mL Chem-Elut cartridge was wetted with 5% aq HCl (6 mL) and allowed to stand for 5 min. The reaction mixture was applied to the cartridge and eluted with ether (20 mL). The eluate was evaporated to dryness and the residue was purified by preparative HPLC to afford N1′(2-adamantyl)-N2-methyl-1H-spiro[isoquinoline-4,4′-piperidine]-1′,2(3H)-dicarboxamide (7.7 mg, 44%). LC-MS Method 1 tR=1.77 min, m/z=437; 1H NMR (CDCl3) δ=1.60-2.10 (18H), 2.80 (1H), 2.88 (s, 3H), 3.25 (m, 2H), 3.77 (s, 2H), 3.88 (d, 2H), 3.98 (s, 1H), 4.52 (s, 2H), 4.87 (1H), 7.05-7.40 (4H).

Workup

  1. waitto stand for 5 min
  2. washeluted with ether (20 mL)
  3. customThe eluate was evaporated to dryness
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-26a1ef71a43145298cb55ed0ca42b4a7
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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