Triethylamine → HCID 57386670, compound

HRID 1965141Notes

Reaction equation

HRID 1965141 reaction equation
Br[C:2]1[CH:19]=[C:18]2[C:5]([CH2:6][C:7]3([C:11]42[N:15]=[C:14]([NH2:16])[C:13]([CH3:17])=[N:12]4)[CH2:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=1.[CH3:20][C:21]([CH3:25])([CH3:24])[C:22]#[CH:23].C(N(CC)CC)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][C:21]([CH3:25])([CH3:24])[C:22]#[C:23][C:2]1[CH:19]=[C:18]2[C:5]([CH2:6][C:7]3([C:11]42[N:15]=[C:14]([NH2:16])[C:13]([CH3:17])=[N:12]4)[CH2:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 135123,3-Dimethyl-1-butyneHCID 573866666'-Bromo-5''-methyl-3'H-dispiro[cyclobutane-1,2'-indene-1',2''-imidazol]-4''-amine

Product 1

HCID 57386670HCID 57386670, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 6′-bromo-5″-methyl-3′H-dispiro[cyclobutane-1,2′-indene-1′,2″-imidazol]-4″-amine (Example 54, 0.100 g, 0.31 mmol) in DMF (10 mL) under argon was added 3,3-dimethyl-but-1-yne (0.039 g, 0.47 mmol), tetrakis(triphenylphosphine)palladium(0) (0.036 g, 0.03 mmol) and triethylamine (1.31 mL, 9.43 mmol). The reaction mixture was stirred at r.t. for 5 min before addition of cuprous iodide (8.98 mg, 0.05 mmol). The reaction mixture was stirred overnight at 65° C. and then partitioned between sat aq. NaHCO3 and EtOAc. The organic phase was dried over MgSO4 and concentrated to give a crude product which was purified by preparative chromatography to afford the title compound (0.039 g, 38% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 1.24 (s, 9 H), 1.47-1.66 (m, 4 H), 1.73-1.84 (m, 1 H), 2.09-2.17 (m, 1 H), 2.18 (s, 3 H), 3.16 (d, 2 H), 6.53 (d, 1 H), 6.60 (s, 2 H), 7.14 (dd, 1 H), 7.24 (d, 1 H); MS (ES+) m/z 320 [M+H]+.

Workup

  1. custompartitioned
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. customto give a crude product which
  5. customwas purified by preparative chromatography

Sources & evidence

ORD record
ord-51625fc01b644ec3887da5eb86ef0991
Source dataset
uspto-grants-2013_04
Patent number
US08415483B2

Reaction notes

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