Triethylamine → N-[4-(3-Dimethylamino-prop-1-ynyl)-3-trifluoromethyl-phenyl]-2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl)-acetamide

HRID 1660975ノート

反応式

HRID 1660975 の反応式
CCCP(=O)=O.[N:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=O)=[CH:18][CH:17]=2)[CH:8]=1.[CH3:26][N:27]([CH3:42])[CH2:28][C:29]#[C:30][C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][C:32]=1[C:38]([F:41])([F:40])[F:39].CCN(CC)CC>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[CH3:42][N:27]([CH3:26])[CH2:28][C:29]#[C:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:23](=[O:25])[CH2:22][C:19]2[CH:18]=[CH:17][C:16]([N:9]3[C:10]4=[N:11][CH:12]=[CH:13][CH:14]=[C:15]4[N:7]=[CH:8]3)=[CH:21][CH:20]=2)=[CH:33][C:32]=1[C:38]([F:39])([F:40])[F:41]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 16167369Propylphosphoric anhydrideHCID 53213084(4-Imidazo[4,5-b]pyridin-3-yl-phenyl)-acetic acidHCID 670216344-(3-Dimethylamino-prop-1-ynyl)-3-trifluoromethyl-phenylamine

生成物 1

HCID 11993289N-[4-(3-Dimethylamino-prop-1-ynyl)-3-trifluoromethyl-phenyl]-2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl)-acetamide

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Propylphosphonic anhydride (50% in DMF, 0.69 mL, 1.19 mmol, 2 equiv) is added to a solution of (4-imidazo[4,5-b]pyridin-3-yl-phenyl)acetic acid (Step 7.1) (0.150 g, 0.59 mmol), 4-(3-dimethylamino-prop-1-ynyl)-3-trifluoromethyl-phenylamine (0.138 g, 0.57 mmol, 0.95 equiv), DMAP (10 mg), and Et3N (0.82 mL, 5.93 mmol, 10 equiv) in DMF (2.0 mL), at rt and under an argon atmosphere. The reaction mixture is stirred at rt for 18 h, diluted with EtOAc and washed with H2O. The aqueous layer is extracted with EtOAc. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by reversed phase MPLC (CH3CN/H2O/TFA) to provide the title compound as a white solid: ES-MS: 477.9 [M+H]+; single peak at tR=3.20 min (System 1); Rf=0.06 (CH2Cl2/NH3 (2 N in MeOH), 95:5).

後処理

  1. washwashed with H2O
  2. extractionThe aqueous layer is extracted with EtOAc
  3. washThe combined organic phase is washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by reversed phase MPLC (CH3CN/H2O/TFA)

出典と根拠

ORDレコード
ord-f507071e7c6b4b928074fc53565ed08b
出典データセット
uspto-grants-2011_10
特許番号
US08030311B2

反応ノート

読み込み中…