Ammonium Chloride → HCID 136358430, compound

HRID 601385Notes

Reaction equation

HRID 601385 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:4](=[O:17])[C:3]=1[C:18]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([NH:28][S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[N+:38]([O-])=O)(=[O:31])=[O:30])=[CH:27][C:21]=2[S:20](=[O:42])(=[O:41])[N:19]=1.[NH4+].[Cl-]>CO.O1CCCC1.O.[Fe]>[NH2:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[S:29]([NH:28][C:26]1[CH:25]=[CH:24][C:22]2[NH:23][C:18]([C:3]3[C:4](=[O:17])[N:5]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]4[C:11]([C:2]=3[OH:1])=[CH:10][CH:9]=[CH:8][N:7]=4)=[N:19][S:20](=[O:42])(=[O:41])[C:21]=2[CH:27]=1)(=[O:31])=[O:30]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 136358431HCID 136358431, compound

Product 1

HCID 136358430HCID 136358430, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the product of Example 409A (8 mg, 0.013 mmol), iron powder (5.0 mg, 0.089 mmol), and NH4Cl (1Mg, 0.019 mmol) in methanol:tetrahydrofuran:water (2:2:1,10 mL) was heated at 60° C. for 2 hour. The solution filtered through Celite® and washed with THF. The solution was concentrated and the residue was diluted with water, and extracted with ethyl acetate. The organic layer was washed with water, dried with MgSO4, filtered and concentrated to give title compound (7 mg, 92%). 1H NMR (300 MHz, DMSO-d6) δ 0.97 (d, J=6.62 Hz, 6 H) 1.54 (m, 2 H) 1.68 (m, 1 H) 4.46 (m, 2 H) 6.06 (s, 2 H) 6.59 (t, J=7.17 Hz, 1 H) 6.78 (d, J=8.46 Hz, 1 H) 7.23 (m, 1 H) 7.46 (m, 4 H) 7.63 (d, J=8.82 Hz, 1 H) 8.53 (dd, J=8.09, 1.84 Hz, 1 H) 8.87 (dd, J=4.41, 1.84 Hz, 1 H) 10.79 (s, 1 H) 14.00 (s, 1 H). (ESI−) m/z 581 (M−H)−.

Workup

  1. filtrationThe solution filtered through Celite®
  2. washwashed with THF
  3. concentrationThe solution was concentrated
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2056f79fa16640fcaf55df86f2346e91
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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