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Diisopropylethylamine → HCID 86716497, compound

HRID 1501324
Notes
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Reaction equation

HRID 1501324 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.[NH2:29][C:30]1[N:31]=[N:32][C:33]([Br:37])=[CH:34][C:35]=1[Br:36].C(N(CC)C(C)C)(C)C>C(O)(C)C>[C:23]1([C:2]2[N:31]3[N:32]=[C:33]([Br:37])[CH:34]=[C:35]([Br:36])[C:30]3=[N:29][C:3]=2[C:5]2[CH:6]=[CH:7][C:8]([C:11]3([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:12][CH2:13][CH2:14]3)=[CH:9][CH:10]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 462384024,6-Dibromopyridazin-3-amineHCID 86691038tert-Butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate

Product 1

HCID 86716497HCID 86716497, compoundYield 28%

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 (5.80 g, 13.1 mmol), 3-amino-4,6-dibromopyridazine (CAS Registry No. 1206487-35-5, 3.96 g, 15.7 mmol, 1.2 eq), N,N-diisopropylethylamine (2.3 mL, 13.0 mmol, 1.0 eq) and powdered activated 3 Å molecular sieves (10 g) in isopropanol (70 mL) was heated at the reflux temperature for 8 h. On cooling, the mixture was filtered through a pad of Celite. The Celite was washed with DCM, and the combined organics were washed with water, dried with sodium sulfate and concentrated under reduced pressure. The remaining material was purified using MPLC (Biotage Isolera; 100 g SNAP cartridge: 100% hexane 2.0 min., gradient to 75% hexane/25% EtOAc 2.5 min., 75% hexane/25% EtOAc 4.5 min., gradient to 50% hexane/50% EtOAc 2 min., 50% hexane/50% EtOAc 4.5 min., gradient to 100% EtOAc 2.5 min., 100% EtOAc 5.7 min.) to give partially purified tert-butyl (1-{4-[3-phenyl-6,8-dibromoimidazo[1,2-b]pyridazin-2-yl]phenyl}cyclobutyl)carbamate (2.65 g, ˜82% pure, 28% yield):

Workup

  1. customwas prepared in a manner analgous to
  2. temperaturewas heated at the reflux temperature for 8 h
  3. temperatureOn cooling
  4. filtrationthe mixture was filtered through a pad of Celite
  5. washThe Celite was washed with DCM
  6. washthe combined organics were washed with water
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe remaining material was purified
  10. customMPLC (Biotage Isolera; 100 g SNAP cartridge: 100% hexane 2.0 min., gradient to 75% hexane/25% EtOAc 2.5 min., 75% hexane/25% EtOAc 4.5 min., gradient to 50% hexane/50% EtOAc 2 min., 50% hexane/50% EtOAc 4.5 min., gradient to 100% EtOAc 2.5 min., 100% EtOAc 5.7 min.)

Sources & evidence

ORD record
ord-012a116d5f63477fa4a26954a045c90c
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09206185B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes