Diisopropylethylamine → HCID 66745858, compound

HRID 1959386Notes

Reaction equation

HRID 1959386 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]#[CH:23])=[N:20][C:19]([N:24]2[CH2:29][CH2:28][N:27]([S:30]([CH2:33][CH3:34])(=[O:32])=[O:31])[CH2:26][CH2:25]2)=[CH:18][N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[N:36]([C:39]1[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=1)=[N+:37]=[N-:38].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].CCN(C(C)C)C(C)C>CC(O)(C)C.O>[C:11]([O:10][C:9]([N:8]([C:16]1[C:21]([C:22]2[N:38]=[N:37][N:36]([C:39]3[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=3)[CH:23]=2)=[N:20][C:19]([N:24]2[CH2:29][CH2:28][N:27]([S:30]([CH2:33][CH3:34])(=[O:31])=[O:32])[CH2:26][CH2:25]2)=[CH:18][N:17]=1)[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:15])([CH3:12])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 162112104-Azidoaniline hydrochlorideHCID 23667548Sodium AscorbateHCID 86662075HCID 86662075, compound

Product 1

HCID 66745858HCID 66745858, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A mixture of tert-butyl N-tert-butoxycarbonyl-N-[5-(4-ethylsulfonylpiperazin-1-yl)-3-ethynyl-pyrazin-2-yl]carbamate (50 mg, 0.1009 mmol) and 4-Azidoaniline hydrochloride (17.32 mg, 0.1009 mmol) were suspended in t-BuOH (1 mL)/Water (1.000 mL). The reaction was treated with (+)-Sodium L-ascorbate (1.999 mg, 0.01009 mmol) followed by CuSO4.5H2O (0.2519 mg, 0.1103 μL, 0.001009 mmol) and the mixture allowed to stir at ambient temperature for 16 hours. The reaction was treated with DIPEA (13.04 mg, 17.57 μL, 0.1009 mmol) and allowed to heat to 40° C. for 5 hours and then cooled to ambient temperature. The mixture was partitioned between EtOAc/NaHCO3 and the aqueous layer extracted with EtOAc (2×), dried (MgSO4), filtered and concentrated. The material was used crude in the next step (quantitative yield assumed). MS (ES+) 630.00

Workup

  1. temperatureto heat to 40° C. for 5 hours
  2. temperaturecooled to ambient temperature
  3. customThe mixture was partitioned between EtOAc/NaHCO3
  4. extractionthe aqueous layer extracted with EtOAc (2×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-156235476cab49579b698ec8a09c4249
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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