Isopropylamine → HCID 67386587, compound

HRID 1898616Notes

Reaction equation

HRID 1898616 reaction equation
[C:1]([CH:3]1[CH2:6][N:5]([C:7](=[O:39])[C@H:8]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=4)[C:25](O)=[O:26])[N:20]=3)[N:15]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:14]=2)=[O:12])[CH3:9])[CH2:4]1)#[N:2].CN(C(ON1N=[N:55][C:50]2[CH:51]=CC=N[C:49]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)(C)C>CN(C=O)C>[C:1]([CH:3]1[CH2:4][N:5]([C:7](=[O:39])[C@H:8]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:30]=[CH:29][CH:28]=[C:24]([C:25](=[O:26])[NH:55][CH:50]([CH3:51])[CH3:49])[CH:23]=4)[N:20]=3)[N:15]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:37])([CH3:36])[CH3:38])[CH:14]=2)=[O:12])[CH3:9])[CH2:6]1)#[N:2]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58438624HCID 58438624, compound

Product 1

HCID 67386587HCID 67386587, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[7-[(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethylcarbamoyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-benzoic acid (70 mg, 0.13 mmol) and HATU (53.4 mg, 0.14 mmol) in DMF (1.5 mL) was added isopropylamine (44 μL, 0.51 mmol). The reaction mixture was stirred at room temp for 4 h then quenched with water and extracted with EtOAc (2×). The combined organics were washed with water (3×) and brine then dried over MgSO4 and concentrated. The residue was chromatographed with 50% to 100% EtOAc/hexanes to isolate 52 mg (69%) of 2-(3-isopropylcarbamoyl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide as an off-white foamy solid.

Workup

  1. customthen quenched with water
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organics were washed with water (3×) and brine
  4. dry with materialthen dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed with 50% to 100% EtOAc/hexanes

Sources & evidence

ORD record
ord-416e5d6df3e2430ba4f15bea4c2b97f7
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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