Hydrochloric Acid → HCID 58204425, compound

HRID 1498369Notes

Reaction equation

HRID 1498369 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][C:20]([C:22]5[N:26]([CH2:27][CH2:28][O:29]C6CCCCO6)[C:25]([CH3:36])=[N:24][CH:23]=5)=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:37]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH:38]([N:41]1[C:45]([C:46]2[N:47]=[C:48]3[C:54]4[CH:55]=[CH:56][C:57]([C:59]5[N:60]=[C:61]([CH3:73])[N:62]([CH2:64][CH2:65][O:66]C6CCCCO6)[CH:63]=5)=[CH:58][C:53]=4[O:52][CH2:51][CH2:50][N:49]3[CH:74]=2)=[N:44][CH:43]=[N:42]1)([CH3:40])[CH3:39].Cl>CO>[CH:38]([N:41]1[C:45]([C:46]2[N:47]=[C:48]3[C:54]4[CH:55]=[CH:56][C:57]([C:59]5[N:60]=[C:61]([CH3:73])[N:62]([CH2:64][CH2:65][OH:66])[CH:63]=5)=[CH:58][C:53]=4[O:52][CH2:51][CH2:50][N:49]3[CH:74]=2)=[N:44][CH:43]=[N:42]1)([CH3:40])[CH3:39].[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][C:20]([C:22]5[N:26]([CH2:27][CH2:28][OH:29])[C:25]([CH3:36])=[N:24][CH:23]=5)=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:37]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 58204593HCID 58204593, compoundHCID 58204787HCID 58204787, compound

Product 2

HCID 58204425HCID 58204425, compoundYield 72%HCID 58204582HCID 58204582, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The mixture of 2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-9-(2-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (left above) and 2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-9-(2-methyl-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-4-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (right above) (90 mg, 0.18 mmol) was dissolved in methanol (3 mL) and a HCl solution in MeOH (4 mol/L, 3.0 mL) was added dropwise at 0° C. The mixture was allowed to warm up to room temperature slowly and stirred at room temperature for 2 h. It was concentrated and the residue was washed with EtOAc to give 255 (65 mg, 72%) and 301 (20 mg, 21%) as HCl salts. 301: 1H NMR (CDCl3, 400 MHz): δ 8.54 (d, J=8.4 Hz, 1H), 7.85 (s, 1H), 7.66 (s, 1H), 7.24 (d, J=8.4 Hz, 2H), 7.11 (s, 1H), 6.89 (s, 1H), 6.04-5.95 (m, 1H), 4.51-4.45 (m, 4H), 4.12-4.06 (m, 2H), 3.78-3.74 (m, 2H), 2.44 (s, 3H), 1.60 (d, J=6.4 Hz, 6H). LC-MS m/z 420 [M+H+]

Workup

  1. concentrationIt was concentrated
  2. washthe residue was washed with EtOAc

Sources & evidence

ORD record
ord-d66a80cc7a544e22bb43a7fac1c8fdf6
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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