Diisopropylethylamine → HCID 22258319, compound

HRID 2244127Notes

Reaction equation

HRID 2244127 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 22258319HCID 22258319, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-7acb728466fa46b493ba5604cef37536
Source dataset
uspto-grants-2010_03
Patent number
US07678812B2

Reaction notes

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