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

HRID 1660975노트

반응식

HRID 1660975 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f507071e7c6b4b928074fc53565ed08b
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030311B2

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