Diisopropylethylamine → HCID 86716495, compound

HRID 1501321Notes

Reaction equation

HRID 1501321 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.[F:29][C:30]([F:39])([F:38])[C:31]1[N:36]=[N:35][C:34]([NH2:37])=[CH:33][CH:32]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[C:23]1([C:2]2[N:35]3[N:36]=[C:31]([C:30]([F:38])([F:29])[F:39])[CH:32]=[CH:33][C:34]3=[N:37][C:3]=2[C:5]2[CH:10]=[CH:9][C:8]([C:11]3([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][CH2:13][CH2:12]3)=[CH:7][CH:6]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 598058596-(Trifluoromethyl)pyridazin-3-amineHCID 86691038tert-Butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate

Product 1

HCID 86716495HCID 86716495, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

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 (1.85 g, ˜80% purity, 3.45 mmol, 1.0 eq), 6-(trifluoromethyl)pyridazin-3-amine (CAS-Nr. 935777-24-5, 0.674 g, 4.14 mmol, 1.2 eq), N,N-diisopropylethylamine (0.60 mL, 6.89 mmol, 1.0 eq) and activated 3 Å molecular sieves in isopropanol (10.5 mL) was heated for 7 hours under reflux. 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; 100 g SNAP cartridge: hexane→hexane/ethyl acetate 2/1) to give 680 mg (34% yield) of the title compound.

Workup

  1. customwas prepared in a manner analgous to
  2. temperaturewas heated for 7 hours
  3. temperatureunder reflux
  4. temperatureOn cooling
  5. customthe mixture was partitioned between DCM and water
  6. filtrationfiltered through a silicone coated filter paper
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe crude mixture was purified via MPLC (Biotage Isolera; 100 g SNAP cartridge: hexane→hexane/ethyl acetate 2/1)

Sources & evidence

ORD record
ord-a1b3492493ec4b0b9880d34011144b1b
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

Loading…