Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 135730580, compound

HRID 354171Notes

Reaction equation

HRID 354171 reaction equation
[CH2:1]([O:5][C:6]1[C:14]([C:15]2[NH:16][C:17](=[O:30])[C:18]3[C:19](=[C:21]([CH2:28][CH3:29])[N:22]([CH2:24][CH2:25][O:26][CH3:27])[N:23]=3)[N:20]=2)=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.Cl.[CH3:64][NH:65][O:66][CH3:67]>ClCCl>[CH2:1]([O:5][C:6]1[C:14]([C:15]2[NH:16][C:17](=[O:30])[C:18]3[C:19](=[C:21]([CH2:28][CH3:29])[N:22]([CH2:24][CH2:25][O:26][CH3:27])[N:23]=3)[N:20]=2)=[CH:13][C:9]([C:10]([N:65]([O:66][CH3:67])[CH3:64])=[O:12])=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 27960291-Hydroxybenzotriazole hydrate2×HCID 135730603HCID 135730603, compound

Product 1

HCID 135730580HCID 135730580, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Butoxy-5-[3-ethyl-2-(2-methoxyethyl)-7-oxo-6,7-dihydro-2H-pyrazolo-[4,3-d]pyrimidin-5-yl]nicotinic acid (Example 3) (200 mg, 0.48 mmol) was dissolved in dichloromethane and 1-hydroxybenzotriazole hydrate (78 mg, 0.58 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (120 mg, 0.58 mmol) were added followed by diisopropylethylamine (0.34 mL, 1.95 mmol). N,O-dimethylhydroxyl-amine hydrochloride (56.3 mg, 0.58 mmol) was added and the mixture stirred at room temperature for 14 h. A further 0.29 mmol of 1-hydroxybenzotriazole hydrate and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride were added and the reaction stirred for a further 3 h. The reaction mixture was diluted with further dichloromethane, washed with water, dried (MgSO4) and concentrated. Purification by flash column chromatography (gradient elution from dichloromethane to 5% methanol:dichloromethane) gave the title compound (178 mg, 81%).

Workup

  1. stirringthe reaction stirred for a further 3 h
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification
  6. washby flash column chromatography (gradient elution from dichloromethane to 5% methanol:dichloromethane)

Sources & evidence

ORD record
ord-783b843d82064139995b30f5b644d62f
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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