Diisopropylethylamine → HCID 67187460, 화합물

HRID 885974

반응식

HRID 885974 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([C:10]3[S:11][C:12]4[C:13](=[O:21])[NH:14][C:15]([CH3:20])([CH3:19])[CH2:16][C:17]=4[N:18]=3)[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[CH3:49][N:50]1[CH2:55][CH2:54][CH:53]([C:56](O)=[O:57])[CH2:52][CH2:51]1.CCN(C(C)C)C(C)C>CN(C=O)C.O.CC#N>[CH3:19][C:15]1([CH3:20])[NH:14][C:13](=[O:21])[C:12]2[S:11][C:10]([N:6]3[C:5]4[CH:22]=[CH:23][C:2]([NH:1][C:56]([CH:53]5[CH2:54][CH2:55][N:50]([CH3:49])[CH2:51][CH2:52]5)=[O:57])=[CH:3][C:4]=4[O:9][CH2:8][CH2:7]3)=[N:18][C:17]=2[CH2:16]1

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)HCID 67185695HCID 67185695, 화합물

생성물 1

HCID 67187460HCID 67187460, 화합물수율 51.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of Example 233 (0.049 g, 0.15 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.111 g, 0.29 mmol) and 1-methylpiperidine-4-carboxylic acid hydrochloride (0.034 g, 0.19 mmol) in DMF (0.5 mL) was added DIPEA (0.06 mL, 0.35 mmol). The reaction mixture was stirred at r.t. for 16 h. MeCN (1 mL) and water (1 mL) were added. The insoluble material was filtered, and the filtrate concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.035 g, 51%) as a yellow solid. δH (CD3OD) 7.91 (1H, d, J 9.0 Hz), 7.37 (1H, d, J 2.3 Hz), 7.11 (1H, dd, J 8.9 and 2.3 Hz), 4.40-4.30 (2H, m), 4.20-4.09 (2H, m), 3.62 (2H, d, J 12.6 Hz), 3.17-3.02 (2H, m), 2.92 (3H, s), 2.89 (2H, s), 2.76-2.60 (1H, m), 2.34-1.91 (4H, m), 1.39 (6H, s). Exchangeable protons were not observed. LCMS (ES+) 456.21 (M+H)+, RT 1.80 minutes (Method 1).

후처리

  1. filtrationThe insoluble material was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by preparative HPLC (Method 6)

출처 및 근거

ORD 기록
ord-fcbfc1827857424ba3909b4ecdeac4af
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242116B2

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