Triethylamine → 6-oxo-N-(quinolin-3-yl)-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxamide

HRID 1521761Notes

Reaction equation

HRID 1521761 reaction equation
[O:1]=[C:2]1[NH:8][CH2:7][CH2:6][CH2:5][N:4]2[C:9]3[N:15]=[C:14]([C:16]([OH:18])=O)[CH:13]=[CH:12][C:10]=3[CH:11]=[C:3]12.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:52][C:53]1[CH:54]=[N:55][C:56]2[C:61]([CH:62]=1)=[CH:60][CH:59]=[CH:58][CH:57]=2.C(N(CC)CC)C>CN(C=O)C>[O:1]=[C:2]1[NH:8][CH2:7][CH2:6][CH2:5][N:4]2[C:9]3[N:15]=[C:14]([C:16]([NH:52][C:53]4[CH:54]=[N:55][C:56]5[C:61]([CH:62]=4)=[CH:60][CH:59]=[CH:58][CH:57]=5)=[O:18])[CH:13]=[CH:12][C:10]=3[CH:11]=[C:3]12

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 113753-AminoquinolineHCID 2724699PyBOPHCID 672363426-Oxo-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acid2×

Product 1

HCID 532421996-oxo-N-(quinolin-3-yl)-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxamideYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3′,2′:4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acid (Intermediate E, 75 mg, 0.31 mmol) and PyBOP (175 mg, 0.34 mmol) in DMF (2 mL) is stirred for 30 min. 3-Aminoquinoline (49 mg, 0.34 mmol) and triethylamine (171 μL, 1.22 mmol) are added and the reaction is stirred at room temperature for 16 h. The mixture is purified via preparative HPLC using a gradient elution from 10-75% acetonitrile/H2O with 0.1% TFA to afford the title compound (93 mg, 82%). LCMS: 372.20 (M+H+). (Method V)

Workup

  1. customThe mixture is purified via preparative HPLC
  2. washa gradient elution from 10-75% acetonitrile/H2O with 0.1% TFA

Sources & evidence

ORD record
ord-67da636374b444da931ba3ad8e699692
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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