HCID 15541340, compound → HCID 9829510, compound

HRID 723448Notes

Reaction equation

HRID 723448 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:39]=[CH:38][C:8]([O:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[S:35])[CH2:33][CH3:34])[O:27][C:26]4=[O:36])=[CH:21][C:20]=3[F:37])[CH2:15][CH2:14]2)=[O:12])=[CH:7][CH:6]=1)[CH3:3].[CH:40]1(C(SCC)=S)CC1>C(N(CC)CC)C>[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:29][C@H:28]([CH2:30][NH:31][C:32]([CH:33]5[CH2:40][CH2:34]5)=[S:35])[O:27][C:26]4=[O:36])=[CH:21][C:20]=3[F:37])[CH2:15][CH2:14]2)=[O:12])=[CH:38][CH:39]=1)[CH3:3]

Participants

4

Reactant 2

HCID 15541340HCID 15541340, compoundHCID 58745346HCID 58745346, compound

Product 1

HCID 9829510HCID 9829510, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

As described for the preparation of 27, the reaction of 26 (prepared from 357 mg of 25) with ethyl cyclopropanecarbodithioate and triethylamine gave the thioamide which was mixed with saturated NaHCO3 and extracted with CH2Cl2. The extract was dried (MgSO4) and concentrated. Chromatography of the residue on silica gel with 5% MeOH-0.5% NH4OH—CH2Cl2 and crystallization of the product from Et2O—CH2Cl2-heptane gave 74 mg of 28: mp 169–170° C.; 1H NMR [300 MHz, (CD3)2SO] δ 0.84 (m, 2H), 1.01 (m, 2H), 2.12 (s, 7H), 2.93. 3.00 (s, s, 4H), 3.25 (s, 2H), 3.60 (s, 4H), 3.79 (dd, 1H), 3.94 (m, 2H), 4.12 (t, 1H), 4.83 (s, 2H), 4.92 (m, 1H), 6.86 (d, 2H), 7.07 (t, 1H), 7.17 (m, 3H), 7.49 (dd, 1H).

Sources & evidence

ORD record
ord-67a60adc254a4a479dec518e451debf3
Source dataset
uspto-grants-2006_11
Patent number
US07141570B2

Reaction notes

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