Potassium Carbonate → HCID 86700320, compound

HRID 879501Notes

Reaction equation

HRID 879501 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:12](=[O:17])[NH:13][CH2:14][CH2:15][N:16]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Br[C:19]1[S:20][C:21]2[C:27]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)=[C:26]([C@H:35]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:25]([CH3:46])=[CH:24][C:22]=2[N:23]=1.COCCOCCN(CCOCCOC)CCOCCOC.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1.[Cu]Cl>[C:42]([O:41][C@@H:35]([C:26]1[C:25]([CH3:46])=[CH:24][C:22]2[N:23]=[C:19]([N:13]3[CH2:14][CH2:15][N:16]=[C:11]([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:2]([CH3:1])[N:3]=[CH:4]5)[C:12]3=[O:17])[S:20][C:21]=2[C:27]=1[C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:36]([O:38][CH2:39][CH3:40])=[O:37])([CH3:43])([CH3:44])[CH3:45]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetateHCID 86700317HCID 86700317, compound

Product 1

HCID 86700320HCID 86700320, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

The mixture of 3-(1-methyl-1H-indazol-5-yl)-5,6-dihydropyrazin-2(1H)-one (160 mg, 0.70 mmol), (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (500 mg, 1.05 mmol), tris(2-(2-methoxyethoxy)ethyl)amine (60 μL, 0.2 mmol), potassium carbonate (320 mg, 2.3 mmol), and copper(I) chloride (69 mg, 0.70 mmol) in xylene (16 mL) was degassed with nitrogen, and was heated at 140° C. for 16 hours. The reaction mixture was cooled and diluted with ethyl acetate. The mixture was filtered through a pad of celite and washed with ethyl acetate. The organic solution was washed with water and brine, and was dried over sodium sulfate. Concentration and purification with flash column chromatography (hexanes/EtOAc) gave (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxo-5,6-dihydropyrazin-1(2H)-yl)benzo[d]thiazol-6-yl)acetate. LCMS-ESI+: calc'd for C34H34ClN5O4S: 644.2 (M+H+); Found: 644.3 (M+H+); and (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxopyrazin-1(2H)-yl)benzo[d]thiazol-6-yl)acetate (40 mg). LCMS-ESI+: calc'd for C34H33ClN5O4S: 642.2 (M+H+); Found: 642.3 (M+H+).

Workup

  1. customwas degassed with nitrogen
  2. temperatureThe reaction mixture was cooled
  3. additiondiluted with ethyl acetate
  4. filtrationThe mixture was filtered through a pad of celite
  5. washwashed with ethyl acetate
  6. washThe organic solution was washed with water and brine
  7. dry with materialwas dried over sodium sulfate
  8. concentrationConcentration and purification with flash column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-8022477664a14b019aaa4c705e0f84b5
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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