Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86630186, compound

HRID 1038131Notes

Reaction equation

HRID 1038131 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[N:8]=[C:7]2[C:32]([OH:34])=O)([O-:3])=[O:2].CN([C:38]([O:42][N:43]1N=NC2C=CC=N[C:44]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CNOC.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:38][O:42][N:43]([CH3:44])[C:32]([C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:9]([C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]=1)=[O:34]

Participants

7

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86630185HCID 86630185, compound

Product 1

HCID 86630186HCID 86630186, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-nitro-1-trityl-1H-indazole-3-carboxylic acid 20AP (12.06 g, 26.85 mmol) and HATU (10.2 g, 26.85 mmol) was dissolved in DMF (100 ml). After stirring for 10 min at room temperature, N,O-dimethylhydroxylamine hydrochloride 21AP (2.62 g, 26.85 mmol) and DIEA (14.1 ml, 80.55 mmol) was added. It was stirred further for 1 hr at room temperature. Reaction mixture was poured into 300 ml of water. Solid was collected by filtration. This solid was redissolved in EtOAc (300 ml) and 75 ml of sat. NaHCO3 was added. Organic fraction was washed with water (2×75 ml), brine (75 ml) and dried over MgSO4. Solvent was removed under reduced pressure to give desired 5-nitro-1-trityl-1H-indazole-3-carboxylic acid methoxy-methyl-amide 22AP (12.56 g, 95%).

Workup

  1. stirringIt was stirred further for 1 hr at room temperature
  2. customReaction mixture
  3. filtrationSolid was collected by filtration
  4. dissolutionThis solid was redissolved in EtOAc (300 ml)
  5. addition75 ml of sat. NaHCO3 was added
  6. washOrganic fraction was washed with water (2×75 ml), brine (75 ml)
  7. dry with materialdried over MgSO4
  8. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9ff5cee9eb984a1bb25f90f92d9cab89
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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