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

HRID 1371631노트

반응식

HRID 1371631 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d180ec2d2e048b08c8cf227a59f28d2
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157455B2

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