HCID 86719142, compound → HCID 70913502, compound

HRID 1844755Notes

Reaction equation

HRID 1844755 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2[N:24]([CH2:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[C:23]([CH3:32])=[C:22]([S:33]([NH:36]C(=O)OCCCC)(=[O:35])=[O:34])[CH:21]=2)=[CH:12]1)(=[O:10])=[O:9]>CO.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2[N:24]([CH2:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[C:23]([CH3:32])=[C:22]([S:33]([NH2:36])(=[O:34])=[O:35])[CH:21]=2)=[CH:12]1)(=[O:9])=[O:10]

Participants

3

Reactant 1

HCID 86719142HCID 86719142, compound

Product 1

HCID 70913502HCID 70913502, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

Crude intermediate 52 (0.50 mmol) was dissolved in dry MeOH/HCl under N2. The mixture was stirred overnight at rt, concentrated, treated with 3% aq. K2CO3, extracted with DCM, dried over Na2SO4, filtered, concentrated and purified by prep-HPLC to afford compound 53 (95 mg, 35%). 1H-NMR (DMSO-d6, 400 MHz) δ: 0.50-0.62 (2H, m), 0.83-0.95 (3H, m), 1.13-1.39 (3H, m), 1.41-1.50 (3H, m), 2.47 (3H, s), 3.81 (2H, d, J=5.6 Hz), 6.47 (1H, s), 7.00 (2H, s), 7.30-7.39 (2H, m), 7.50-7.54 (1H, m), 7.68-7.80 (4H, m), 8.00 (1H, s), 8.38-8.42 (1H, m). MS Calcd.: 545; MS Found: 546 (M+1).

Workup

  1. concentrationconcentrated
  2. additiontreated with 3% aq. K2CO3
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-0164ab8ca14540b996e11dfb87ad152d
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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