Hydrochloric Acid → 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-9-(1-methyl-5-(piperidin-3-yl)-1H-pyrazol-4-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

HRID 1530606Notes

Reaction equation

HRID 1530606 reaction equation
C(O1C[CH2:11][CH2:10][CH:9]([C:13]2[N:17]([CH3:18])[N:16]=[CH:15][C:14]=2[C:19]2[CH:20]=[C:21]3[C:30](=[CH:31][CH:32]=2)[C:29]2[N:25]([CH:26]=[C:27]([C:33]4[N:37]([CH:38]([CH3:40])[CH3:39])[N:36]=[C:35]([CH3:41])[N:34]=4)[N:28]=2)[CH2:24][CH2:23][O:22]3)[CH2:8][NH:7][C:6]1=O)(C)(C)C.Cl.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:41][C:35]1[N:34]=[C:33]([C:27]2[N:28]=[C:29]3[N:25]([CH:26]=2)[CH2:24][CH2:23][O:22][C:21]2[C:30]3=[CH:31][CH:32]=[C:19]([C:14]3[CH:15]=[N:16][N:17]([CH3:18])[C:13]=3[CH:9]3[CH2:10][CH2:11][CH2:6][NH:7][CH2:8]3)[CH:20]=2)[N:37]([CH:38]([CH3:39])[CH3:40])[N:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 178432608HCID 178432608, compound

Product 1

HCID 683127572-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-9-(1-methyl-5-(piperidin-3-yl)-1H-pyrazol-4-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepineYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-tert-butyl-5-(1-methyl-4-{4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}-1H-pyrazol-5-yl)-λ3,3-oxazocan-2-one (540 mg, 0.94 mmol) in MeOH (10 mL) was added 4N HCl (2 mL). The reaction mixture was stirred at room temperature for 4 h. 1N K2CO3 (6.0 mL) was added. After concentration, the residue was purified by reverse phase Combiflash eluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3 to afford 4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-12-[1-methyl-5-(piperidin-3-yl)-1H-pyrazol-4-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (320 mg, 72% yield). LCMS (ESI) m/z: 473.4 [M+H+]

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by reverse phase Combiflash
  3. washeluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record
ord-48011206183f4bcd863b448a76da90f9
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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