Dimethylamine → HCID 57731589、化合物

HRID 2234697ノート

反応式

HRID 2234697 の反応式
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]

参加物

7

反応物 4

HCID 674DimethylamineHCID 14797Potassium HydroxideHCID 81531DiisopropylethylamineHCID 57731571HCID 57731571、化合物

生成物 1

HCID 57731589HCID 57731589、化合物収率 35%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-91d8926342fb4419bb0fff786c37f9d4
出典データセット
uspto-grants-2010_05
特許番号
US07709645B2

反応ノート

読み込み中…