HCID 67426900, compound → HCID 59489903, compound

HRID 1808036Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=O)[C:11](=[CH:20]N(C)C)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[NH:25]([C@@H:29]1[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]1)[C:26]([NH2:28])=[NH:27]>>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3[N:27]=[C:26]([NH:25][C@@H:29]4[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]4)[N:28]=[CH:20][C:11]=3[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Reactant 2

HCID 67426900HCID 67426900, compound

HCID 178451959HCID 178451959, compound

Product 1

HCID 59489903HCID 59489903, compoundYield 57%

Procedure

This product was prepared by using (R)-4-(3,4-dichlorophenyl)-2-((dimethylamino)methylene)-3,4-dihydronaphthalen-1(2H)-one and (R)-tert-butyl 3-guanidinopiperidine-1-carboxylate hydrochloride salt under the condition described in the general procedure 1 to afford the desired product in 57% yield as a light yellow solid. M.p.=85-87° C. 1H NMR 400 MHz (DMSO-d6) δ 8.29 (bs, 1 H), 8.12 (s, 1 H), 7.50-7.35 (m, 4 H), 7.08 (s, 1 H), 7.02-6.98 (m, 2 H), 4.39 (t, J=5.2 Hz, 1 H), 3.74 (bs, 2 H), 3.12-3.04 (m, 2 H), 2.90-2.84 (m, 2 H), 1.89-1.51 (m, 3 H), 1.38-1.24 (m, 11 H). LCMS m/e 525 (M+H).

Workup

customThis product was prepared

Sources & evidence

ORD record: ord-c517898c05754cdf87055fd9dcd64073
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357694B2

Reaction notes

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