5-Hydroxyindole → HCID 59394040, compound

HRID 1887663Notes

Reaction equation

HRID 1887663 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][C:9]2[N:10]=[CH:11][N:12]=[C:13](Cl)[C:8]=2[CH2:7]1)=[O:5])[CH3:2].[OH:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]=[CH:28]2.C1CCN2C(=NCCC2)CC1>CC#N>[CH2:1]([O:3][C:4]([CH:6]1[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][C:9]2[N:10]=[CH:11][N:12]=[C:13]([O:24][C:25]3[CH:26]=[C:27]4[C:31](=[CH:32][CH:33]=3)[NH:30][CH:29]=[CH:28]4)[C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 160545-HydroxyindoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59394014HCID 59394014, compound

Product 1

HCID 59394040HCID 59394040, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-chloro-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-6,7-dicarboxylic acid 7-tert-butyl ester 6-ethyl ester (1 g, 2.93 mmol) in CH3CN (30 mL), 5-hydroxy-indole (0.779 g, 5.85 mmol) and DBU (0.88 mL, 5.85 mmol) are added. After heating at 60° C. for 5 h the reaction is evaporated and the product isolated using FCC eluting with heptane:EtOAc 1:1. MS (ESI) m/z 439.1 (M+1).

Workup

  1. customis evaporated
  2. customthe product isolated
  3. washeluting with heptane:EtOAc 1:1

Sources & evidence

ORD record
ord-fe4cf6e92fc3440cab06e5c41e9369a6
Source dataset
uspto-grants-2013_08
Patent number
US08501756B2

Reaction notes

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