Hydrochloric Acid → HCID 66953757, compound

HRID 1424597Notes

Reaction equation

HRID 1424597 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CCN(C(C)C)C(C)C.[CH:15]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH:16]1[NH:25][C:26]([N:28]1[CH2:33][CH2:32][C:31]3([C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH2:36][NH:35][CH2:34]3)[CH2:30][CH2:29]1)=[O:27])[CH2:22]2.Cl>C(Cl)Cl>[CH:15]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH:16]1[NH:25][C:26]([N:28]1[CH2:33][CH2:32][C:31]3([C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH2:36][N:35]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:34]3)[CH2:30][CH2:29]1)=[O:27])[CH2:22]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 25064399N-(2-adamantyl)-2,3-dihydro-1H-spiro[isoquinoline-4,4'-piperidine]-1'-carboxamide

Product 1

HCID 66953757HCID 66953757, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A vial, equipped with a flea stir bar, was charged with methanesulfonyl chloride (4.5 μL, 58 μmol), DIEA (15 μL, 90 μmol) and CH2Cl2 (1 mL). A solution of N-(2-adamantyl)-2,3-dihydro-1H-spiro[isoquinoline-4,4′-piperidine]-1′-carboxamide (25 mg, 53 μmol) in CH2Cl2 (1 mL) was added and the mixture was stirred overnight. 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 N-(2-adamantyl)-2-(methylsulfonyl)-2,3-dihydro-1H-spiro[isoquinoline-4,4′-piperidine]-1′-carboxamide (8 mg, 33%). LC-MS Method 1 tR=1.89 min, =458; 1H NMR (CDCl3) δ=1.60-2.15 (18H), 2.92 (s, 3H), 3.13 (m, 2H), 3.51 (s, 2H), 3.90 (d, 2H), 3.99 (s, 1H), 4.45 (s, 2H), 4.88 (1H), 7.05-7.40 (4H).

Workup

  1. customA vial, equipped with a flea
  2. stirringthe mixture was stirred overnight
  3. washeluted with ether (20 mL)
  4. customThe eluate was evaporated to dryness
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4f054c63dcf54a519689d19467e876fb
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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