Ammonia → HCID 18391707, compound

HRID 617303Notes

Reaction equation

HRID 617303 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:7][C@H:6]([CH3:8])[CH2:5][C@H:4]1[CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.N.CO>CCOCC>[ClH:1].[ClH:1].[CH3:2][N:3]1[CH2:7][C@H:6]([CH3:8])[CH2:5][C@H:4]1[CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric Acid2×HCID 887MethanolHCID 18391708HCID 18391708, compound

Product 1

HCID 18391707HCID 18391707, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of HCl in ether was added dropwise to a stirred solution of compound 24b (55 mg, 0.27 mmol) in diethyl ether at room temperature. The resultant white precipitate was then collected by centrifugation and triturated with three portions of diethyl ether. The hygroscopic solid was obtained in 56% yield (42 mg). mp 223-225° C. MS m/e (DCI/NH3): 207 (M+H+). 1H NMR (DMSO-d6, 300 MHz) δ: 8.65 (d, J=2.9 Hz, 1H), 8.46 (d, J=5.9 Hz, 1H), 8.00 (dd, J=2.3, 8.7 Hz, 1H), 7.81 (dd, J=5.2, 8.7 Hz, 1H), 4.60 (dd, J=8.1, 11.0 Hz, 1H), 4.49 (dd, J=3.5, 10.4 Hz, 1H), 4.04-3.95 (m, 1H), 3.64-3.58 (m, 1H), 2.92 (s, 3H), 2.80-2.74 (m, 1H), 2.45-2.40 (m, 1H), 2.04-1.98 (m, 1H), 1.95-1.89 (m, 1H), 1.07 (d, J=6.9 Hz, 3H). Anal. Calc. for C12H18N2O.2.0 HCl: C, 51.62; H, 7.22; N, 10.03. Found: C, 51.84; H, 7.36; N, 9.90. [α]D =-2.3° (c=0.32, MeOH).

Workup

  1. customThe resultant white precipitate was then collected by centrifugation
  2. customtriturated with three portions of diethyl ether
  3. customThe hygroscopic solid was obtained in 56% yield (42 mg)

Sources & evidence

ORD record
ord-2380a4e6fce140ada0d366f95fffaf87
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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