1,4-Dioxane → HCID 21934519, compound

HRID 1241435Notes

Reaction equation

HRID 1241435 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4][CH:5]([C:10]1[S:14][C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[N:12][CH:11]=1)[CH2:6][C:7]([O-:9])=[O:8].[N:23]1[C:32]2[NH:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:26]=[CH:25][C:24]=1[CH2:33][CH2:34][CH2:35][C:36](=[S:38])[NH2:37].O1CCO[CH2:41][CH2:40]1>>[ClH:1].[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[S:14][C:10]([CH:5]([CH2:4][C:3]3[N:37]=[C:36]([CH2:35][CH2:34][CH2:33][C:24]4[CH:25]=[CH:26][C:27]5[CH2:28][CH2:29][CH2:30][NH:31][C:32]=5[N:23]=4)[S:38][CH:2]=3)[CH2:6][C:7]([O:9][CH2:40][CH3:41])=[O:8])=[CH:11][N:12]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 21934496HCID 21934496, compoundHCID 21934528HCID 21934528, compound

Product 1

HCID 21934519HCID 21934519, compoundYield 44%

Conditions

Temperature
120 °C

Procedure

thyl 6-chloro-3-[2-(4-chlorophenyl)-1,3-thiazol-5-yl]-5-oxohexanoate, Scheme 2, Example A, (230 mg, 0.595 mmol) and 4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butanethioamide, Scheme 3, Step 1, (140 mg, 0.595 mmol) was dissolved in 1,4-dioxane (5 mL) and heated to 120° C. for 18 hours. The solvent was removed and the residue purified via reverse phase HPLC to give the product (180 mg, 44%). 1H NMR (DMSO-d6) δ1.10 (t, 3H), 1.77–1.85 (m, 2H), 2.02–2.11 (m, 2H), 2.68–2.90 (m, 6H), 2.95–3.18 (m, 4H), 3.38–3.46 (m, 2H), 3.86–3.95 (m, 2H), 4.00 (q, 2H), 6.55 (d, 1H), 7.18 (s, 1H), 7.48–7.55 (m, 2H), 7.57 (d, 1H), 7.62 (s, 1H), 7.80–7.85 (m, 2H).

Workup

  1. customThe solvent was removed
  2. customthe residue purified via reverse phase HPLC

Sources & evidence

ORD record
ord-5712e9bc34794c7cb0a79ed2a42e1e25
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

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