Ammonia → HCID 18391710, compound

HRID 617304Notes

Reaction equation

HRID 617304 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:7][C@H:6]([CH2:8][CH3:9])[CH2:5][C@H:4]1[CH2:10][O:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.N.CO>CCOCC>[ClH:1].[ClH:1].[CH3:2][N:3]1[CH2:7][C@H:6]([CH2:8][CH3:9])[CH2:5][C@H:4]1[CH2:10][O:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric Acid2×HCID 887MethanolHCID 18391711HCID 18391711, compound

Product 1

HCID 18391710HCID 18391710, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of hydrochloride in ether was added dropwise to a stirred solution of compound 25b (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 219-220° C. MS m/e (DCI/NH3): 221 (M+H+). 1H NMR (D2O, 300 MHz) δ: 8.45 (d, J=2.6 Hz, 1H), 8.36 (d, J=5.1 Hz, 1H), 7.91 (m, 1H), 7.76 (dd, J=5.2, 8.8 Hz, 1H), 4.59 (dd, J=2.9, 11.0 Hz, 1H), 4.43 (dd, J=5.9, 11.0 Hz, 1H), 4.04-3.95 (m, 1H), 4.08-4.00 (m, 1H), 3.83 (dd, J=6.6, 11.0 Hz), 3.05 (s, 3H), 2.95 (t, J=11.0 Hz, 1H), 2.45-2.00 (m, 2H), 2.14-2.03 (m, 1H), 1.60-1.45 (m, 2H), 0.94 (t, J=7.4 Hz, 3H). Anal, Calcd. for C13H20N2O.1.9 HCl: C, 53.92; H, 7.62; N, 9.67. Found: C, 54.00; H, 7.59; N, 9.35. [α]D =-1.9° (c 0.37, 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-824d200000e04b5ca280f58b88a2161a
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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