Sodium t-butoxide → HCID 178481620, compound

HRID 707373Notes

Reaction equation

HRID 707373 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:13])[C:9](=O)[O:10]C.[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH:23][C@H:24]1[CH2:27][C@H:26]([NH2:28])[CH2:25]1.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH:23][C@H:24]1[CH2:25][C@H:26]([N:28]2[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N:8]([CH3:13])[C:9]2=[O:10])[CH2:27]1

Participants

6

Reactant 3

HCID 23676156Sodium t-butoxideHCID 86694143HCID 86694143, compoundHCID 178511738HCID 178511738, compound2×

Product 1

HCID 178481620HCID 178481620, compoundYield 12.69%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Following the procedure described for Example 44 (MethOD B6), using methyl (2-bromophenyl)(methyl)carbamate, INTERMEDIATE 74 (0.510 g, 2.089 mmol), trans-N1-(benzo[d]thiazol-2-yl)cyclobutane-1,3-diamine, INTERMEDIATE 11 (0.400 g, 1.824 mmol), tris(dibenzylideneacetone)dipalladium (o) (0.042 g, 0.046 mmol), 2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-triisopropyl-1,1′biphenyl (0.049 g, 0.091 mmol), and sodium tert-butoxide (0.351 g, 3.65 mmol) in dry dioxane (5 mL) afforded the title compound 1-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one (0.0811 g, 0.231 mmol, 12.69% yield) m/z: 351.0 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) δ: ppm 2.55-2.65 (m, 2 H) 3.38-3.47 (m, 5 H) 4.47-4.55 (m, 1 H) 5.22 (quin, J=8.51 Hz, 1 H) 6.97-7.01 (m, 1 H) 7.06-7.16 (m, 4 H) 7.27-7.33 (m, 1 H) 7.57 (d, J=8.02 Hz, 1 H) 7.60 (dd, J=7.92, 0.68 Hz, 1 H).

Sources & evidence

ORD record
ord-11baa691430243f7a5074bec73b5b67c
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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