Diisopropylethylamine → HCID 70817949, compound

HRID 1501362Notes

Reaction equation

HRID 1501362 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(=O)OC(C)(C)C)[CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=O.[NH2:29][C:30]1[N:35]=[N:34][C:33]([C:36]([O:38][CH3:39])=[O:37])=[C:32]([CH3:40])[C:31]=1[CH3:41].C(N(CC)C(C)C)(C)C>C(#N)CCC>[NH2:15][C:11]1([C:8]2[CH:9]=[CH:10][C:5]([C:3]3[N:29]=[C:30]4[C:31]([CH3:41])=[C:32]([CH3:40])[C:33]([C:36]([O:38][CH3:39])=[O:37])=[N:34][N:35]4[C:2]=3[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:6][CH:7]=2)[CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 71742688HCID 71742688, compoundHCID 86691038tert-Butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate

Product 1

HCID 70817949HCID 70817949, compoundYield 16%

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] (630 mg, ˜90% purity, 1.28 mmol, 1.0 eq), methyl 6-amino-4,5-dimethylpyridazine-3-carboxylate [that was prepared in a manner analgous to that described for Intermediate Example Int-34] (257 mg, 1.28 mmol, 1.0 eq), N,N-diisopropylethylamine (220 μL, 1.28 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 preparative reversed phase HPLC to give 89 mg (16% yield) of the title compound directly as the free amine.

Workup

  1. customthat was prepared in a manner analgous to
  2. customthat was prepared in a manner analgous to
  3. temperatureOn cooling the mixture
  4. customwas partitioned between DCM and water
  5. filtrationfiltered through a silicone coated filter paper
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe crude mixture was purified via preparative reversed phase HPLC

Sources & evidence

ORD record
ord-6758f2bf03c44e6c906c87feebf1a810
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

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