O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 74222540, compound

HRID 1624131Notes

Reaction equation

HRID 1624131 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([OH:18])=O)=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[NH2:24][CH:25]([CH3:32])[CH:26]([OH:31])[C:27]([F:30])([F:29])[F:28].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>ClCCl>[F:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:24][CH:25]([CH:26]([OH:31])[C:27]([F:30])([F:29])[F:28])[CH3:32])=[O:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 10844496HCID 10844496, compoundHCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 74222540HCID 74222540, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

250 mg of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid (0.785 mmol), 112 mg of 3-amino-1,1,1-trifluorobutan-2-ol (mixture of four stereoisomers; 0.785 mmol) and 277 mg of TBTU (0.864 mmol) were dissolved in 1.5 ml of dichloromethane, and the mixture was stirred at RT for 48 h. The reaction mixture was concentrated and the residue was taken up in methanol and purified by preparative HPLC (Method 7). This gave 186 mg (53% of theory) of the title compound, which was separated by preparative HPLC on a chiral phase.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by preparative HPLC (Method 7)
  3. customThis gave 186 mg (53% of theory) of the title compound, which was separated by preparative HPLC on a chiral phase

Sources & evidence

ORD record
ord-8e545243da5c4f4b8c9966b5bd0a48f2
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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