O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 58386531, compound

HRID 74667Notes

Reaction equation

HRID 74667 reaction equation
C(C1C(C(O)=O)=CC(N2CCC(N3C4C(=NC=CC=4)NC3=O)CC2)=NC=1)#N.[C:28]([C:30]1[C:31]([N:39]2[CH2:44][CH2:43][CH:42]([N:45]3[C:53]4[C:48](=[N:49][CH:50]=[CH:51][CH:52]=4)[NH:47][C:46]3=[O:54])[CH2:41][CH2:40]2)=[CH:32][C:33]([C:36](O)=[O:37])=[N:34][CH:35]=1)#[N:29].Cl.Cl.[CH3:57][C:58]1([CH3:67])[CH2:63][NH:62][CH2:61][C:60]2[CH:64]=[N:65][NH:66][C:59]1=2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:57][C:58]1([CH3:67])[CH2:63][N:62]([C:36]([C:33]2[N:34]=[CH:35][C:30]([C:28]#[N:29])=[C:31]([N:39]3[CH2:40][CH2:41][CH:42]([N:45]4[C:53]5[C:48](=[N:49][CH:50]=[CH:51][CH:52]=5)[NH:47][C:46]4=[O:54])[CH2:43][CH2:44]3)[CH:32]=2)=[O:37])[CH2:61][C:60]2[CH:64]=[N:65][NH:66][C:59]1=2

Participants

6

Reactant 4

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58386393HCID 58386393, compoundHCID 58386557HCID 58386557, compoundHCID 667221937,7-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride

Product 1

HCID 58386531HCID 58386531, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.11 mg (0.29 mmol) of an isomer mixture of 5′-cyano-4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4′-carboxylic acid and 5′-cyano-4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-2′-carboxylic acid, 65 mg (0.29 mmol) 7,7-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride and 0.17 mL (1.2 mmol) TEA were placed in 1.5 mL DMF. 0.10 g (0.32 mmol) TBTU were added. The reaction mixture was stirred over the weekend at RT. The purification and separation of the isomers were carried out by HPLC-MS. The product-containing fractions were combined and freeze-dried.

Workup

  1. customThe purification and separation of the isomers
  2. customfreeze-dried

Sources & evidence

ORD record
ord-e2d2cc7f3b594df296356776aafa9f83
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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