Diisopropylethylamine → HCID 86716516, compound

HRID 1501343Notes

Reaction equation

HRID 1501343 reaction equation
Br[CH:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=O.[Cl:29][C:30]1[N:35]=[N:34][C:33]([NH2:36])=[C:32]([CH3:37])[C:31]=1[CH3:38].C(N(CC)C(C)C)(C)C>C(#N)CCC>[Cl:29][C:30]1[C:31]([CH3:38])=[C:32]([CH3:37])[C:33]2[N:34]([C:2]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([C:11]4([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][CH2:13][CH2:12]4)=[CH:7][CH:6]=3)[N:36]=2)[N:35]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 69919433-Amino-6-chloro-4,5-dimethylpyridazineHCID 86691038tert-Butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate

Product 1

HCID 86716516HCID 86716516, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of crude tert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate [that was prepared in a manner analgous to that described for Intermediate Example Int-1-A] (237 mg, ˜80% purity, 0.430 mmol, 1.0 eq), 6-chloro-4,5-dimethylpyridazin-3-amine (CAS-Nr. 76593-36-7, 67.2 mg, 0.430 mmol, 1.0 eq) and N,N-diisopropylethylamine (70 μL, 0.430 mmol, 1.0 eq) in butyronitrile (2.6 mL) was heated for 17 hours at 125° C. On cooling the mixture was partitioned between DCM and water, stirred vigorously and filtered through a silicone coated filter paper. The filtrate was concentrated in vacuo. The crude mixture was purified via MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/EtOAc 9/1→hexane/EtOAc 3/2) to give 185 mg (78% yield) of the title compound.

Workup

  1. customthat was prepared in a manner analgous to
  2. temperatureOn cooling the mixture
  3. customwas partitioned between DCM and water
  4. filtrationfiltered through a silicone coated filter paper
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe crude mixture was purified via MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/EtOAc 9/1→hexane/EtOAc 3/2)

Sources & evidence

ORD record
ord-53f2f2901f2e43248ea8194f1f6ed635
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

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