HCID 59713676, compound → HCID 10196661, compound

HRID 2223084Notes

Reaction equation

HRID 2223084 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([N:14]=[C:15]=[S:16])[N:8]=[C:7]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[C:6]=2[CH:23]=1.[N:24]1([C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]([NH2:40])=[CH:32][CH:31]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([NH:14][C:15]([NH:40][C:33]3[C:34]4[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:30]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:31][CH:32]=3)=[S:16])[N:8]=[C:7]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[C:6]=2[CH:23]=1

Participants

3

Reactant 2

HCID 59713676HCID 59713676, compoundHCID 59713770HCID 59713770, compound

Product 1

HCID 10196661HCID 10196661, compoundYield 56%

Procedure

A solution of 7-chloro-1,3-dihydro-3-isothiocyanato-1-methyl-5-(3-pyridinyl)-2H-1,4-benzodiazepin-2-one (0.0282 g, 0.0823 mmol) and 4-(4-morpholinyl)-1-naphthalenamine (0.0188 g, 0.0823 mmol) in (CH2Cl)2 (2.5 mL) was heated at 70° C. for 24 h. The reaction was cooled and concentrated in vacuo, and the residue was purified by silica gel column chromatography (1:2 CH2Cl2:EtOAc) to provide the title compound (0.0263 g, 56%). 1H-NMR (CDCl3): δ 8.72-8.68 (m, 2H), 8.29-8.25 (m, 1H), 8.11-8.07 (m, 1H), 8.05-8.00 (m, 2H), 7.64-7.55 (m, 5H), 7.38-7.33 (m, 3H), 7.15 (d, J=8.0 Hz, 1H), 6.08 (d, J=7.6 Hz, 1H), 4.03-3.96 (br m, 4H), 3.39 (s, 3H), 3.15 (br s, 4H). HRMS calculated for (C30H27ClN6O2S+H) (M+H)+: 571.1683. Found (ESI): 571.1699. Anal. Calcd for C30H27ClN6O2S+0.7 H2O: C, 61.73; H, 4.90; N, 14.40. Found: C, 61.93;H, 4.79; N, 13.87.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. customthe residue was purified by silica gel column chromatography (1:2 CH2Cl2:EtOAc)

Sources & evidence

ORD record
ord-0db27936fc304f869c377975cec71592
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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