N,N-Dimethylglycine → 1-[4-[4-Amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidin-1-yl]-2-dimethylamino-ethanone

HRID 1435210Notes

Reaction equation

HRID 1435210 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([OH:7])=O)[CH3:3].O.ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.FC(F)(F)C(O)=O.[NH2:50][C:51]1[C:56]([C:57]([C:59]2[CH:64]=[C:63]([F:65])[CH:62]=[CH:61][C:60]=2[O:66][CH3:67])=[O:58])=[CH:55][N:54]=[C:53]([NH:68][CH:69]2[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]2)[N:52]=1.C(N(CC)CC)C>CN(C)C=O>[NH2:50][C:51]1[C:56]([C:57](=[O:58])[C:59]2[CH:64]=[C:63]([F:65])[CH:62]=[CH:61][C:60]=2[O:66][CH3:67])=[CH:55][N:54]=[C:53]([NH:68][CH:69]2[CH2:74][CH2:73][N:72]([C:5](=[O:7])[CH2:4][N:2]([CH3:3])[CH3:1])[CH2:71][CH2:70]2)[N:52]=1

Participants

7

Reactant 5

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 21070627[4-Amino-2-(piperidin4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone trifluoroacetic acid salt

Product 1

HCID 103204781-[4-[4-Amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidin-1-yl]-2-dimethylamino-ethanoneYield 30.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N,N-dimethylaminoacetic acid (9.8 mg, 0.095 mmol, Aldrich) in dimethylformamide (2 mL) were added 1-hydroxybenzotriazole hydrate (16.5 mg, 0.108 mmol, Aldrich), O-benzotriazol-1-yl-N,N, N′,N′-tetramethyluronium hexafluorophosphate (40.8 mg, 0.108 mmol, Aldrich). After it was stirred for 20 minutes, a solution of [4-amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone trifluoroacetic acid salt (47 mg, Example 59) and triethylamine (47 mg, 0.469 mmol, Aldrich) in dimethylformamide (2 mL) were added. The mixture was stirred overnight at room temperature before it was concentrated, taken up in ethyl acetate, washed with brine and evaporated. The crude product was purified on HPLC to give 1-[4-[4-amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidin-1-yl]-2-dimethylamino-ethanone (12.5 mg). MS (M+H)+: 431.

Workup

  1. stirringThe mixture was stirred overnight at room temperature before it
  2. concentrationwas concentrated
  3. washwashed with brine
  4. customevaporated
  5. customThe crude product was purified on HPLC

Sources & evidence

ORD record
ord-85d83f038e4542329cc32a9d6d982a17
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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