O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 1-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-2'-carbonyl]-1,2,2a,5-tetrahydro-3H-pyrrolo[4,3,2-de]quinolin-4-one

HRID 74689Notes

Reaction equation

HRID 74689 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]2[NH:7][C:8](=[O:27])[N:9]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[CH:22][N:21]=[C:20]([C:24]([OH:26])=O)[CH:19]=4)[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[NH:30]1[C:40]2[C:41]3[CH:32]([CH2:33][C:34](=[O:42])[NH:35][C:36]=3[CH:37]=[CH:38][CH:39]=2)[CH2:31]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]2[NH:7][C:8](=[O:27])[N:9]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[CH:22][N:21]=[C:20]([C:24]([N:30]5[C:40]6[C:41]7[CH:32]([CH2:33][C:34](=[O:42])[NH:35][C:36]=7[CH:37]=[CH:38][CH:39]=6)[CH2:31]5)=[O:26])[CH:19]=4)[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 104421921,2,2a,5-Tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-oneHCID 583864784-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-2'-carboxylic acid

Product 1

HCID 583867461-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-2'-carbonyl]-1,2,2a,5-tetrahydro-3H-pyrrolo[4,3,2-de]quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

67 mg (0.17 mmol) 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-2′-carboxylic acid and 30 mg (0.17 mmol) 1,2,2a,5-tetrahydro-3H-pyrrolo[4,3,2-de]quinolin-4-one in 56 μL (0.40 mmol) TEA and 1.8 mL DMF were combined with 58 mg (0.18 mmol) TBTU and stirred overnight 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-1d38c20e0e6e432e830a8649c7afd2bf
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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