Dimethylamine → HCID 57731589, 화합물

HRID 2234697노트

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HRID 2234697 반응식
C(OC([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]3[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])=[CH:27][N:26](S(C4C=CC(C)=CC=4)(=O)=O)[C:23]3=[N:24][CH:25]=2)[CH:15]=1)C(O)=O)=O)(C)(C)C.[CH3:47][NH:48][CH3:49].[CH:50](N(C(C)C)CC)(C)C.[OH-:59].[K+]>CN(C=O)C.CO>[NH2:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]3[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])=[CH:27][NH:26][C:23]3=[N:24][CH:25]=2)[CH:15]=1)[C:47]([N:48]([CH3:50])[CH3:49])=[O:59]

참가 물질

7

반응물 4

HCID 674DimethylamineHCID 14797Potassium HydroxideHCID 81531DiisopropylethylamineHCID 57731571HCID 57731571, 화합물

생성물 1

HCID 57731589HCID 57731589, 화합물수율 35%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-tert-butoxycarbonylamino-3-{3-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-propionic acid (100 mg, 0.16 mmol), dimethylamine (2 N solution in THF, 0.16 mL, 0.32 mmol), diisopropylethylamine (24 mg, 0.19 mmol) in DMF (1 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,N′-tetramethyluronium hexafluorophosphate (73 mg, 0.19 mmol). The resulting solution was stirred at room temperature for 1 hour. Methanol (1 mL) and potassium hydroxide (50% w/v in water, 0.2 mL) were added and the resulting mixture was stirred for 30 minutes. The mixture was concentrated under reduced pressure. To the residue was added trifluoroacetic acid (1 mL) and the resulting mixture was sonicated until the residue is completely dissolved. The solution was concentrated and the residue purified by mass-triggered reverse-phase HPLC to afford 2-amino-3-{3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-propionamide as a pale yellow solid (23 mg, 35%). MS: m/z 415 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 2.77 (s, 3H), 2.82 (s, 3H), 2.77 (dd, 1H), 2.89 (dd, 1H), 3.84 (s, 3H), 7.05 (t, 1H), 7.14 (d, 1H), 7.19 (d, 1H), 7.30 (dt, 1H), 7.38 (t, 1H), 7.53 (s, 1H), 7.56 (d, 1H), 7.585 (dd, 1H), 7.73 (d, 1H), 8.15 (d, 1H), 8.53 (d, 1H), 11.87 (s, 1H).

후처리

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionTo the residue was added trifluoroacetic acid (1 mL)
  4. customthe resulting mixture was sonicated until the residue
  5. dissolutionis completely dissolved
  6. concentrationThe solution was concentrated
  7. customthe residue purified by mass-triggered reverse-phase HPLC

출처 및 근거

ORD 기록
ord-91d8926342fb4419bb0fff786c37f9d4
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709645B2

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