Sulfuric Acid → HCID 73775386, compound

HRID 712063Notes

Reaction equation

HRID 712063 reaction equation
CC1C=CC(S(OC[C@H:13]2[CH2:18][CH2:17][C@H:16]([N:19]3[C:23]4=[C:24]5[S:30][CH:29]=[CH:28][C:25]5=[N:26][CH:27]=[C:22]4[N:21]=[C:20]3[CH3:31])[CH2:15][O:14]2)(=O)=O)=CC=1.[C-:32]#N.[Na+].S(=O)(=O)(O)O.C[N:41]([CH:43]=O)C>CO>[CH3:31][C:20]1[N:19]([C@@H:16]2[CH2:15][O:14][C@@H:13]([CH2:32][C:43]#[N:41])[CH2:18][CH2:17]2)[C:23]2=[C:24]3[S:30][CH:29]=[CH:28][C:25]3=[N:26][CH:27]=[C:22]2[N:21]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6228Dimethylformamide2×HCID 8929Sodium CyanideHCID 86717522HCID 86717522, compound

Product 1

HCID 73775386HCID 73775386, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of [(2R,5S)-5-(2-methyl-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl)tetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate (50.2 mg, 0.110 mmol) and sodium cyanide (9.1 mg, 0.19 mmol) in DMF (1.1 mL) was added 1.0 M sulfuric acid in DMF (9 μL, 0.009 mmol). The reaction solution was stirred at 50° C. overnight. After cooling, the mixture was diluted with methanol and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product (15.2 mg, 44%). LCMS calculated for C16H17N4OS (M+H)+: m/z=313.1. Found: 313.0.

Workup

  1. temperatureAfter cooling
  2. custompurified with prep-LCMS (XBridge C18 column
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-e4344d791f8b4e639bbac843b5cddac3
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…