Indoline → HCID 58386528, compound

HRID 74668Notes

Reaction equation

HRID 74668 reaction equation
C(C1[C:4]([C:25](O)=O)=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12](N3C4C(=NC=CC=4)NC3=O)[CH2:11]C2)=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]([OH:38])=O)=[N:34][CH:35]=1)#[N:29].N1C2C(=CC=CC=2)CC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[N:9]1([C:36]([C:33]2[N:34]=[CH:35][C:30]([C:28]#[N:29])=[C:31]([N:39]3[CH2:44][CH2:43][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])[CH2:41][CH2:40]3)[CH:32]=2)=[O:38])[C:6]2[C:12](=[CH:11][CH:25]=[CH:4][CH:5]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 10328IndolineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58386393HCID 58386393, compoundHCID 58386557HCID 58386557, compound

Product 1

HCID 58386528HCID 58386528, 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, 34 mg (0.29 mmol) 2,3-dihydro-1H-indole and 90 μL (0.61 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-861ae8ff0dea4ac0bfbfa90fdc02d042
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

Loading…