Diisopropylethylamine → HCID 67517898, compound

HRID 919627Notes

Reaction equation

HRID 919627 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:21][NH:22][CH:23]1[CH2:29][O:28][CH2:27][CH2:26][N:25]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:24]1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:21][N:22]([C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1)[CH:23]1[CH2:29][O:28][CH2:27][CH2:26][N:25]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:24]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 442289674-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidineHCID 1212238251374243-36-3

Product 1

HCID 67517898HCID 67517898, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (110 mg (0.36 mmol) 107.a, of tert-butyl 6-(methylamino)-1,4-oxazepane-4-carboxylate (84 mg (0.36 mmol) X.3, and DIEA (0.127 mL (0.730 mmol) in DMF (2.8 mL) was heated at 90° C. in a sealed tube for 18 hr. The mixture was diluted with H2O and extracted with EtOAc (2×). The combined organics were washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo, absorbing onto 4 g SiO2. Purification by flash column chromatography (ISCO 24 g SiO2, 10% EtOAc/hexanes then gradient to 80% EtOAc/hexanes) afforded tert-butyl 6-(methyl-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-1,4-oxazepane-4-carboxylate (0.142 g) 107.4 as a yellow glassy solid. LCMS (ESI) m/z: 502.20 [M+H]+.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organics were washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customabsorbing onto 4 g SiO2
  7. customPurification by flash column chromatography (ISCO 24 g SiO2, 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-14c8529b8c154c94a243e8ca96b84b2b
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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