Methyl 4-bromo-3-(methoxymethyl)benzoate → HCID 46909205, compound

HRID 1631023Notes

Reaction equation

HRID 1631023 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=O)=[CH:4][C:3]=1[CH2:12][O:13]C.O[N:16]=[C:17]([C:19]1[CH:20]=[N:21][C:22]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:23][CH:24]=1)[NH2:18]>>[CH3:9][O:8][CH2:6][C:5]1[CH:4]=[C:3]([C:12]2[O:13][N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[N:21][CH:20]=3)[N:16]=2)[CH:2]=[CH:11][C:10]=1[C:2]1[CH:11]=[CH:10][CH:5]=[CH:4][C:3]=1[CH3:12]

Participants

3

Reactant 2

HCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoateHCID 74313861HCID 74313861, compound

Product 1

HCID 46909205HCID 46909205, compound

Procedure

The title compound was prepared following procedure described in Method B starting from Intermediate A1 and N′-hydroxy-6-pyrrolidin-1-ylpyridine-3-carboximidamide (UkrOrgSynthesis, BBV-073346). After purification by flash chromatography (silica, EtOAc/cHex) followed by a crystallization from a mixture of MTBE and heptane, the title compound was obtained as an off-white powder. HPLC (Method A), Rt: 4.1 min (purity: 99%). UPLC/MS, M+(ESI): 417.1, M−(ESI): 415.2. Elemental analysis: [C26H26N4O2-0.2H20] calculated: C, 72.60%; H, 6.19%; N, 13.03%. found: C, 72.68%; H, 6.45%; N, 13.05%.

Workup

  1. customThe title compound was prepared following procedure
  2. customAfter purification by flash chromatography (silica, EtOAc/cHex)
  3. customfollowed by a crystallization from a mixture of MTBE and heptane

Sources & evidence

ORD record
ord-64f1f29414394d188081f7f4ff617fa1
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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