Triethylamine → HCID 178492663, compound

HRID 245636Notes

Reaction equation

HRID 245636 reaction equation
[Br:1][C:2]1[C:6]2=[CH:7][C:8]([Cl:30])=[C:9]3[C:14]([C:13](=[O:15])[O:12][C:11]([C:16]4[N:17]([C:23]5[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=5)[N:18]=[C:19]([O:21][CH3:22])[CH:20]=4)=[N:10]3)=[C:5]2[NH:4][N:3]=1.Cl.[C:32]1([NH2:38])([CH:35]2[CH2:37][CH2:36]2)[CH2:34][CH2:33]1.C(N(CC)CC)C>CN(C)C=O>[C:32]1([NH:38][C:13]([C:14]2[C:9]([NH:10][C:11]([C:16]3[N:17]([C:23]4[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=4)[N:18]=[C:19]([O:21][CH3:22])[CH:20]=3)=[O:12])=[C:8]([Cl:30])[CH:7]=[C:6]3[C:5]=2[NH:4][N:3]=[C:2]3[Br:1])=[O:15])([CH:35]2[CH2:37][CH2:36]2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53433499(1,1'-Bi(cyclopropan))-1-amine hydrochlorideHCID 178487785HCID 178487785, compound

Product 1

HCID 178492663HCID 178492663, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 120 mg (0.24 mmol) of the above 3-bromo-5-chloro-7-[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazol-3-yl]-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one in 2.4 mL of N,N-dimethylformamide is added 95 mg (0.71 mmol) of bicyclopropyl-1-ylamine hydrochloride and 99 μL (0.71 mmol) of triethylamine. The reaction is stirred at 50° C. for 24 hours and then concentrated in vacuo. The residue is taken-up with acetone and after filtration the filtrate is evaporated. Purification of the residue by flash chromatography (SiO2, hexanes/ethyl acetate 1:1) affords 80 mg (56%) of a solid; LC/MS:606/608 (M+H)+, m.p.: 190-194° C.

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationafter filtration the filtrate
  3. customis evaporated
  4. customPurification of the residue by flash chromatography (SiO2, hexanes/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-1340ccd1e70944cba8e10f221a65886f
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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