Ammonium Chloride → HCID 9957839, compound

HRID 427400Notes

Reaction equation

HRID 427400 reaction equation
[C:1]([C:3]1([NH:28][C:29](=[O:47])[CH:30]([CH2:40][CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)[CH2:31][C:32]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[O:33])[CH2:7][CH2:6][N:5]([CH2:8]C2C3C(=CC=CC=3)N(S(C3C=CC(C)=CC=3)(=O)=O)C=2)[CH2:4]1)#[N:2].[NH4+:48].[Cl-]>CO>[C:1]([C:3]1([NH:28][C:29](=[O:47])[CH:30]([CH2:40][CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)[CH2:31][C:32]([N:34]2[CH2:35][CH2:36][O:37][CH2:38][CH2:39]2)=[O:33])[CH2:7][CH2:6][N:5]([CH2:8][C:30]2[NH:48][C:42]3[C:41]([CH:40]=2)=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 20601602HCID 20601602, compound

Product 1

HCID 9957839HCID 9957839, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of N-{3-cyano-1-[1-(toluene-4-sulfonyl)-1H-indole-3-ylmethyl]-pyrrolidin-3-yl}-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyramide (0.052 g, 0.079 mmol) and Mg (powder) (0.038 g, 1.6 mmol) in MeOH (5 mL) was sonicated at room temperature reaction was monitored by MS. When completed, the reaction mixture was poured into a saturated solution of NH4Cl and extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4 and concentrated to provide the title compound in 76% yield. The compound was recrystallized from Et2O/hexanes. 1H NMR (CDCl3) 8.1 (1H, s), 7.71-7.69 (1H, m), 7.39-7.37 (1H, m), 7.25-7.15 (3H, m), 6.9 (1H, s), 4.0-3.8 (2H, m), 3.7-3.3 (11H, m), 3.2-3.1 (1H, m), 3.0-2.5 (3H, m), 2.3-2.15 (2H, m), 1.8-1.4 (5H, m), 1.35-1.03 (5H, m), 0.95-0.78 (3H,m). MS, m/z 506=M+1.

Workup

  1. customwas sonicated at room temperature
  2. customreaction
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cc51a1b6756746058f1654a621e6d857
Source dataset
uspto-grants-2001_11
Patent number
US06313117B1

Reaction notes

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