Pyridine → HCID 57900521, compound

HRID 2079053Notes

Reaction equation

HRID 2079053 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].N1C=CC=CC=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[C:22](=[O:23])[NH:21][N:20]=[C:19]1[C:24]1[S:40][C:27]2[C:28]3[CH:36]=[CH:35][C:34]([C:37](Cl)=[O:38])=[CH:33][C:29]=3[O:30][CH2:31][CH2:32][C:26]=2[CH:25]=1>C1COCC1.O>[NH2:3][CH2:2][CH2:1][NH:4][C:37]([C:34]1[CH:35]=[CH:36][C:28]2[C:27]3[S:40][C:24]([C:19]4[N:18]([C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=5[Cl:11])[C:22](=[O:23])[NH:21][N:20]=4)=[CH:25][C:26]=3[CH2:32][CH2:31][O:30][C:29]=2[CH:33]=1)=[O:38]

Participants

6

Reactant 3

HCID 1049PyridineHCID 3301EthylenediamineHCID 57900387HCID 57900387, compound

Product 1

HCID 57900521HCID 57900521, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethane-1,2-diamine (82 mg, 1.36 mmol) and pyridine (0.5 mL) in 5 mL of THF was slowly added 2-(4-(2-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carbonyl chloride (ca. 417 mg, ca. 0.91 mmol) in 20 mL of THF at 0° C. The mixture was stirred at room temperature overnight, diluted with water and purified by preparative HPLC to afford 66 mg of 533, isolated yield: 20%. ESI-MS: 482. 1H NMR (DMSO-d6, 400 MHz): δ 8.74 (s, 1H, NH), 8.37 (s, 1H, NH), 7.74-7.47 (m, 7H, ArH), 6.47 (s, 1H, ═CH), 4.19 (t, J=4.8 Hz, 2H, CH2), 3.40-3.36 (m, 4H, 2CH2), 2.98 (t, J=5.2 Hz, 2H, CH2), 2.86 (t, J=6.0 Hz, 2H, CH2).

Workup

  1. customat 0° C
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-41405d0e7e40415ea8ffe7b696872723
Source dataset
uspto-grants-2011_04
Patent number
US07928248B2

Reaction notes

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