Ammonium Chloride → HCID 9957839, compound

HRID 480240Notes

Reaction equation

HRID 480240 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 (CDC13) 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 (1H, 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-94cca8e49d204d6f91ffd7ce871d105c
Source dataset
uspto-grants-2003_11
Patent number
US06649642B2

Reaction notes

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