Triethylamine → HCID 73776350, compound

HRID 711993Notes

Reaction equation

HRID 711993 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:12]3=[C:13]4[S:19][CH:18]=[CH:17][C:14]4=[N:15][CH:16]=[C:11]3[N:10]=[C:9]2[C@H:20]([OH:22])[CH3:21])[CH2:4][CH2:3]1.C(N(CC)CC)C.FC(F)(F)S(O[CH2:36][C:37]([F:40])([F:39])[F:38])(=O)=O>C(Cl)Cl>[F:38][C:37]([F:40])([F:39])[CH2:36][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:12]3=[C:13]4[S:19][CH:18]=[CH:17][C:14]4=[N:15][CH:16]=[C:11]3[N:10]=[C:9]2[C@H:20]([OH:22])[CH3:21])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 86717455HCID 86717455, compound

Product 1

HCID 73776350HCID 73776350, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (1R)-1-(1-piperidin-4-yl-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl)ethanol hydrochloride (21.6 mg, 0.0637 mmol) and triethylamine (40.0 μL, 0.287 mmol) in methylene chloride (0.78 mL) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (17.8 mg, 0.0765 mmol). The resulting mixture was stirred overnight at room temperature. The solvents were evaporated, and the crude residue purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give 6.5 mg (26%) of the desired product. LCMS calculated for C17H20F3N4OS (M+H)+: m/z=385.1. Found: 385.0.

Workup

  1. customThe solvents were evaporated
  2. customthe crude residue purified on RP-HPLC (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-c1e50f8884e64314a1a933b74c0e377d
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…