Indoline → 4'-(2,3-dihydro-indole-1-carbonyl)-4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzo-diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrile

HRID 74655Notes

Reaction equation

HRID 74655 reaction equation
[C:1]([C:3]1[C:4]([C:29](O)=[O:30])=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:21][CH2:20][C:19]4[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:18]=4[NH:17][C:16]3=[O:28])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)#[N:2].[NH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[N:32]1([C:29]([C:4]2[C:3]([C:1]#[N:2])=[CH:8][N:7]=[C:6]([N:9]3[CH2:14][CH2:13][CH:12]([N:15]4[CH2:21][CH2:20][C:19]5[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:18]=5[NH:17][C:16]4=[O:28])[CH2:11][CH2:10]3)[CH:5]=2)=[O:30])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 10328IndolineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58386480HCID 58386480, compound

Product 1

HCID 426138694'-(2,3-dihydro-indole-1-carbonyl)-4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzo-diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.02 g (0.48 mmol) 5′-cyano-4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4′-carboxylic acid, 57 mg (0.48 mmol) 2,3-dihydro-1H-indole and 0.21 mL (1.5 mmol) TEA were placed in 3 mL DMF. 0.17 g (0.52 mmol) TBTU were added. The reaction mixture was stirred overnight at RT and then purified by HPLC. The product-containing fractions were combined and freeze-dried.

Workup

  1. custompurified by HPLC
  2. customfreeze-dried

Sources & evidence

ORD record
ord-9b0627472feb4faf8b73b0b60ac2d655
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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