1,2-Dichloroethane → N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-1-[1-(tert-butoxycarbonyl)-(2R)-piperidin-2-ylcarbonyl]-L-prolinamide

HRID 857763노트

반응식

HRID 857763 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([N:33]2[CH:37]=[N:36][N:35]=[N:34]2)=[C:22]([CH:32]=1)[CH2:23][NH:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.CC#N.O>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([N:33]2[CH:37]=[N:36][N:35]=[N:34]2)=[C:22]([CH:32]=1)[CH2:23][NH:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:14]([C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16]

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 688618(2R)-1-[(tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 69655818N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

생성물 1

HCID 69655970N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-1-[1-(tert-butoxycarbonyl)-(2R)-piperidin-2-ylcarbonyl]-L-prolinamide

시약·촉매·용매 3

HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매2회

실험 절차

The title compound was prepared from (2R)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (52 mg, 0.23 mmol), N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (Example 26, Step B, 70 mg, 0.23 mmol, 1.0 equiv), EDC (66 mg, 0.34 mmol, 1.5 equiv) and HOAt (16 mg, 0.11 mmol, 0.5 equiv) in DMF (500 μl) essentially according to the procedure described in Example 26, Step C. Reverse phase HPLC [95:5 water (+0.1% TFA)/CH3CN (+0.1% TFA) to 5:95 water (+0.1% TFA)/CH3CN (+0.1% TFA)] afforded the title compound as a clear oil. 1H NMR (400 MHz, CDCl3): δ 9.16 (s, 1 H), 7.90 (br s, 1 H), 7.59 (s, 1 H), 7.41 (d, J=8.4 Hz, 1 H), 7.24 (d, J =8.4 Hz, 1 H), 4.56 (br s, 1 H), 4.38 (br s, 1 H), 4.18–4.15 (m, 2 H), 3.80 (br s, 1 H), 3.58–3.52 (m, 3 H), 2.15–2.11 (m, 2 H), 2.05–1.98 (m, 2 H), 1.95–1.84 (m, 2 H), 1.70–1.68 (m, 2 H), 1.55 (br s, 2 H), 1.33 (s, 9 H). LCMS (M+H): 518.3.

출처 및 근거

ORD 기록
ord-db805e102f66481dbd8a3b9c48ec7cd3
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144899B2

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