Formic Acid → 8-Chloro-1-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carbaldehyde

HRID 1243599Notes

Reaction equation

HRID 1243599 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1.[CH:28](O)=[O:29]>>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH:28]=[O:29])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[CH:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 113264888-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene

Product 1

HCID 219256578-Chloro-1-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carbaldehyde

Procedure

A solution of the amine from example 4 (300 mg, 0.79 mmol) in formic acid (15 ml) was stirred at 80° C. for 3 hours. The cooled mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and sodium bicarbonate solution. The layers were separated, and the organic phase was evaporated under reduced pressure to give the title compound.

Workup

  1. concentrationThe cooled mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and sodium bicarbonate solution
  3. customThe layers were separated
  4. customthe organic phase was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6581bfb063b74af8ba5d00167153095d
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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