Tert-Butylamine → HCID 57585160, compound

HRID 2077564Notes

Reaction equation

HRID 2077564 reaction equation
[CH3:1][C:2]([NH2:5])([CH3:4])[CH3:3].[H-].[Na+].Cl[C:9]1[N:14]=[C:13]([C:15]2[CH:27]=[CH:26][C:18]3[N:19]=[C:20]([NH:22][C:23](=[O:25])[CH3:24])[S:21][C:17]=3[CH:16]=2)[CH:12]=[N:11][CH:10]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:2]([NH:5][C:9]1[N:14]=[C:13]([C:15]2[CH:27]=[CH:26][C:18]3[N:19]=[C:20]([NH:22][C:23](=[O:25])[CH3:24])[S:21][C:17]=3[CH:16]=2)[CH:12]=[N:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:1]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 24758Sodium hydrideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 51354316HCID 51354316, compound

Product 1

HCID 57585160HCID 57585160, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A microwave vial equipped with a magnetic stir bar was charged with 2-methylpropan-2-amine (0.100 g, 2 mmol) in DMF (3 ml). Then sodium hydride (0.047 g, 2.0 mmol) was added into the mixture and allowed to stir an additional 15 minutes. Then N-(6-(6-chloropyrazin-2-yl)benzo[d]thiazol-2-yl)acetamide (0.100 g, 0.30 mmol), palladium(II) acetate (0.007 g, 0.03 mmol) and Xantphos (0.010 g) was added to the mixture. The vial was capped and placed into a CEM Microwave for 10 minutes at 100° C., while 100 watts of energy was supplied via Powermax® (Simultaneous heating while cooling technology). The progress of the reaction was monitored by LC/MS, which showed desired product in the mixture. The mixture was placed into a round-bottom flask, then diluted with ethyl acetate (20 ml) and stirred 20 minutes. The precipitate was collected by filtration and then purified by reverse-phase HPLC. This gave N-(6-(6-(tert-butylamino)pyrazin-2-yl)benzo[d]thiazol-2-yl)acetamide (0.005 g, 4% yield) as a tan crystalline solid. MS (ESI pos. ion) m/z: 342 (MH+). Calc'd exact mass for C17H19N5OS: 341. 1H NMR 400 MHz, DMSO-d6): 1.49 (s, 9H), 2.09 (s, 3H), 6.80 (s, 1H), 7.62 (d, J=8.03 Hz, 1H), 7.82 (s, 1H), 7.98 (d, J=8.03 Hz, 1H), 8.24 (s, 1H), 8.43 (s, 1H).

Workup

  1. customA microwave vial equipped with a magnetic stir bar
  2. customThe vial was capped
  3. waitplaced into a CEM Microwave for 10 minutes at 100° C., while 100 watts of energy
  4. temperaturewas supplied via Powermax® (Simultaneous heating while cooling technology)

Sources & evidence

ORD record
ord-02fb0b792f234e148d07a76f824da1f2
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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