Dimethylformamide → [4-Amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]methanol

HRID 1094870Notes

Reaction equation

HRID 1094870 reaction equation
CN(C=O)C.[NH2:6][C:7]1[C:12]2=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][N:11]2[N:10]=[CH:9][N:8]=1.[Cl-].[CH2:19]=[N+:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CO>[NH2:6][C:7]1[C:12]2=[CH:13][C:14]([CH2:16][OH:17])=[C:15]([CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:11]2[N:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11367014Morpholinium, 4-methylene-, chlorideHCID 55297730HCID 55297730, compound

Product 1

HCID 57955268[4-Amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]methanolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of DMF (50 mL) was added (4-aminopyrrolo[2,1-f][1,2,4]triazin-6-yl)methanol (550 mg, 3.35 mmol) and 4-methylenemorpholin-4-ium chloride (Eur. J. Med. Chem. 1989, 24, 379-384) (636 mg, 4.69 mmol). The solution was stirred at rt for 1 h and then the solvent was evaporated. The oil was triturated with CH2Cl2 and a white solid was collected. The free based was obtained by stirring over a Dowex 66 solid support resin in MeOH. The material was filtered and evaporated yielding 794 mg (90%) of the desired product as a white solid. MS [M+H]+=264; LCMS RT=1.07.

Workup

  1. customthe solvent was evaporated
  2. customThe oil was triturated with CH2Cl2
  3. customa white solid was collected
  4. customThe free based was obtained
  5. filtrationThe material was filtered
  6. customevaporated

Sources & evidence

ORD record
ord-1ead5a46c03c4f77a6b39716e38b698d
Source dataset
uspto-grants-2012_03
Patent number
US08133995B2

Reaction notes

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