Pyridine → HCID 57900521, compound

HRID 84679Notes

Reaction equation

HRID 84679 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].N1C=CC=CC=1.C1COCC1.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[C:27](=[O:28])[NH:26][N:25]=[C:24]1[C:29]1[S:45][C:32]2[C:33]3[CH:41]=[CH:40][C:39]([C:42](Cl)=[O:43])=[CH:38][C:34]=3[O:35][CH2:36][CH2:37][C:31]=2[CH:30]=1>O>[NH2:3][CH2:2][CH2:1][NH:4][C:42]([C:39]1[CH:40]=[CH:41][C:33]2[C:32]3[S:45][C:29]([C:24]4[N:23]([C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=5[Cl:16])[C:27](=[O:28])[NH:26][N:25]=4)=[CH:30][C:31]=3[CH2:37][CH2:36][O:35][C:34]=2[CH:38]=1)=[O:43]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3301EthylenediamineHCID 8028Tetrahydrofuran2×HCID 57900387HCID 57900387, compound

Product 1

HCID 57900521HCID 57900521, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethane-1,2-diamine (82 mg, 1.36 mmol) and pyridine (0.5 mL) in 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 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-39dc48223cb644ea986c210be4cd3065
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

Loading…