Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-N-methoxy-N-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxamide

HRID 1530669Notes

Reaction equation

HRID 1530669 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](O)=[O:23])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:25]=2)=[N:7][C:6]([CH3:26])=[N:5]1)([CH3:3])[CH3:2].Cl.[CH3:28][O:29][NH:30][CH3:31].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[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]([N:30]([O:29][CH3:28])[CH3:31])=[O:23])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:25]=2)=[N:7][C:6]([CH3:26])=[N:5]1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 683132352-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylic acid

Product 1

HCID 866714762-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-N-methoxy-N-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylic acid (4.00 g, 11.3 mmol) and N-methoxymethanamine hydrochloride (1.32 g, 13.6 mmol) in N,N-Dimethylformamide (100 mL) was added N-Ethyldiisopropylamine 7.9 mL, 45.3 mmol) followed by HBTU (4.72 g, 12.5 mmol). The reaction mixture was stirred at room temperature for 1 hour. LC-MS analysis of the reaction mixture showed no more starting material. The solvent was removed and the residue was diluted with DCM, washed with NaHCO3 sat. aq., dried over Na2SO4, filtered and concentrated. The resulting oil was purified on silica gel (0→10% MeOH/DCM) to give 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-N-methoxy-N-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxamide

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with DCM
  3. washwashed with NaHCO3 sat. aq.
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting oil was purified on silica gel (0→10% MeOH/DCM)

Sources & evidence

ORD record
ord-873352b51ec6412ba77a9e5ff498d028
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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