Ethanol → HCID 11676934, compound

HRID 1371557Notes

Reaction equation

HRID 1371557 reaction equation
FC(F)(F)C([NH:5][C:6]1[C:10]([C:11]2[S:12][C:13]([NH:16][C:17](=[O:30])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][CH2:28]Cl)[CH:20]=3)=[N:14][N:15]=2)=[N:9][O:8][N:7]=1)=O.[NH2:33][CH:34]1[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35]1.CCO>O>[NH:37]1[CH2:38][CH2:39][CH:34]([NH:33][CH2:28][CH2:27][CH2:26][O:25][C:21]2[CH:20]=[C:19]([CH2:18][C:17]([NH:16][C:13]3[S:12][C:11]([C:10]4[C:6]([NH2:5])=[N:7][O:8][N:9]=4)=[N:15][N:14]=3)=[O:30])[CH:24]=[CH:23][CH:22]=2)[CH2:35][CH2:36]1

Participants

5

Reactant 3

HCID 702EthanolHCID 12682914-Amino-1-Boc-piperidineHCID 21071305HCID 21071305, compound

Product 1

HCID 11676934HCID 11676934, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Trifluoroacetyl-4-(5-(3-(3-chloro-propoxy)-phenylacetyl)amino-[1,3,4]thiadiazol-2-yl)-furazan-3-ylamine (0.05 g, 0.1 mmol), 4-amino-N-Boc-piperidine (0.082 g, 0.4 mmol) and EtOH (0.3 mL) were heated by microwave irradiation at 120° C., 10 minutes; 150° C., 10 minutes; and 150° C., 30 minutes. The reaction was diluted with water and purified by preparative HPLC. Yield: 0.02 g (43%). 1H-NMR (MeOD) δ 7.27–7.30 (t, 1H), 6.96–6.98 (m, 2H), 6.88 (d, 1H), 4.14 (t, 2H), 3.87 (s, 2H), 3.50–3.60 (m, 3H), 3.07–3.10 (m, 2H), 2.36–2.39 (m, 2H), 2.17–2.20 (m, 2H), 1.82–1.90 (m, 2H), 1.30–1.35 (m, 2H). LCMS 459.0 (M+1), HPLC Method B Rt 1.7 minutes.

Workup

  1. custom150° C., 10 minutes
  2. custom150° C., 30 minutes
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f121a21eb0194ccdabbfffb4d4c6eda7
Source dataset
uspto-grants-2007_01
Patent number
US07157476B2

Reaction notes

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