Hydrochloric Acid → 1-{2-[((S)-1-{1-[4-(4-Fluoro-phenyl)-1-methyl-1H-pyrazol-3-yl]-methanoyl}-piperidin-2-ylmethyl)-amino]-pyrimidin-5-yl}-ethanone

HRID 18106Notes

Reaction equation

HRID 18106 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][CH2:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]2[C:16]([C:18]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH:21][N:20]([CH3:30])[N:19]=2)=[O:17])=[N:6][CH:7]=1.C([Sn](CC[CH2:42][CH3:43])CCCC)CCC.Cl.[OH2:45]>O1CCOCC1>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]2[C:18]([C:16]([N:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]3[CH2:9][NH:8][C:5]3[N:4]=[CH:3][C:2]([C:42](=[O:45])[CH3:43])=[CH:7][N:6]=3)=[O:17])=[N:19][N:20]([CH3:30])[CH:21]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3032732TributylstannanylHCID 670897601-{(S)-2-[(5-Bromo-pyrimidin-2-ylamino)-methyl]-piperidin-1-yl}-1-[4-(4-fluoro-phenyl)-1-methyl-1H-pyrazol-3-yl]-methanone

Product 1

HCID 670904211-{2-[((S)-1-{1-[4-(4-Fluoro-phenyl)-1-methyl-1H-pyrazol-3-yl]-methanoyl}-piperidin-2-ylmethyl)-amino]-pyrimidin-5-yl}-ethanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-{(S)-2-[(5-Bromo-pyrimidin-2-ylamino)-methyl]-piperidin-1-yl}-1-[4-(4-fluoro-phenyl)-1-methyl-1H-pyrazol-3-yl]-methanone (0.5 g) and 1-ethoxyvinyl)tributyltin (0.42 ml) tetrakis(triphenylphosphine)palladium[0} (0.06 g) was boiled in dioxane (8 ml) for 16 h. 2N Hydrochloric acid was added, the mixture stirred for 90 min, water was added and the mixture extracted (x3) with ethyl acetate. The combined ethyl acetate extracts were dried, solvent removed at reduced pressure and the residue column chromatographed (silica gel, ethyl acetate→2% methanol ethyl acetate to give the title compound (0.3 g) as a yellow foam.

Workup

  1. extractionthe mixture extracted (x3) with ethyl acetate
  2. dry with materialThe combined ethyl acetate extracts were dried
  3. customsolvent removed at reduced pressure
  4. customthe residue column chromatographed (silica gel, ethyl acetate

Sources & evidence

ORD record
ord-0af93e6df8054a5982c33c389ce89d87
Source dataset
uspto-grants-2010_06
Patent number
US07741329B2

Reaction notes

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