Diisopropylethylamine → HCID 22258319, 화합물

HRID 1047201노트

반응식

HRID 1047201 반응식
Cl.[CH2:2]([C@@H:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12][CH2:11][C@@H:10]1[NH2:21])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[N:31]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=1)=[C:32]=[S:33]>C(#N)C>[CH2:2]([CH:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH:10]1[NH:21][C:32]([NH:31][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=1)=[S:33])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 20637794cis-1-Benzyl-6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochlorideHCID 22258323HCID 22258323, 화합물

생성물 1

HCID 22258319HCID 22258319, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of cis-1-benzyl-6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochloride (0.306 g, 1.01 mmol), diisopropylethylamine (0.264 mL, 1.51 mmol) and 4-isothiocyanatomethyl-2-methoxy-1-methoxymethoxy-benzene (0.253 g, 1.06 mmol) in acetonitrile (10 mL) was stirred at ambient temperature overnight. The solvent was evaporated in vacuo, and the residue was purified by reverse phase preparative HPLC, on a C18 column eluted with a gradient of 40 to 90% acetonitrile in water with 0.1% TFA, to give the product, 1-(1-benzyl-6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-3-(3-methoxy-4-methoxymethoxy-benzyl)-thiourea, 0.21 g (41%). 1H NMR (CDCl3): δ 1.64 (br s, 1H), 1.85 (m, 1H), 2.04 (m, 1H), 2.63 (m, 1H), 2.82 (m, 2H), 2.98 (m, 1H), 3.33 (m, 1H), 3.49 (s, 3H), 3.78 (s, 3H), 3.84 (s, 3H), 4.32 (br s, 2H), 5.19 (s, 2H), 5.7 (br s, 1H), 6.0 (br s, 1H), 6.64 (m, 3H), 6.80 (s, 1H), 6.91 (d, J=8.4 Hz, 1H), 7.03 (d, J=8.2 Hz, 1H) and 7.11 to 7.28 (m, 5H). MS: m/z 507 (M+H)+.

후처리

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by reverse phase preparative HPLC, on a C18 column
  3. washeluted with a gradient of 40 to 90% acetonitrile in water with 0.1% TFA

출처 및 근거

ORD 기록
ord-39af3fdbd8d4457697accce393bd7a08
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569505B2

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