O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 42613146, compound

HRID 74693Notes

Reaction equation

HRID 74693 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:27])[CH2:14][CH2:13]1)#[N:2].[F:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][CH2:33][CH2:32]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[F:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[N:34]([C:7]([C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[C:4]([N:12]3[CH2:17][CH2:16][CH:15]([N:18]4[C:26]5[C:21](=[N:22][CH:23]=[CH:24][CH:25]=5)[NH:20][C:19]4=[O:27])[CH2:14][CH2:13]3)[CH:5]=1)=[O:9])[CH2:33][CH2:32]2

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27744635-FluoroindolineHCID 58386571HCID 58386571, compound

Product 1

HCID 42613146HCID 42613146, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

70 mg (0.19 mmol) 4-cyano-3-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-benzoic acid and 30 mg (0.21 mmol) 5-fluoro-2,3-dihydro-(1H)-indole in 0.10 mL (0.72 mmol) TEA and 1.5 mL DMF were mixed with 65 mg (0.20 mmol) TBTU and the mixture was stirred for 1 h at RT. Then the reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. customfreeze-dried

Sources & evidence

ORD record
ord-bf8fcc5207a44824849bf1d6e35061ba
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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