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

HRID 1844211Notes

Reaction equation

HRID 1844211 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-7aa10f1befbd41cfaabd260b40c3bb2a
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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