Trifluoroacetic acid → HCID 178511079, compound

HRID 712024Notes

Reaction equation

HRID 712024 reaction equation
[C:1]([CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([N:10]2[C:14]3=[C:15]4[S:21][CH:20]=[CH:19][C:16]4=[N:17][CH:18]=[C:13]3[N:12]=[C:11]2[CH:22]2[CH2:25][N:24](C([O-])=O)[CH2:23]2)[CH2:6][CH2:5]1)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl.CO>[NH:24]1[CH2:25][CH:22]([C:11]2[N:10]([C@H:7]3[CH2:6][CH2:5][C@H:4]([CH2:3][C:1]#[N:2])[CH2:9][CH2:8]3)[C:14]3=[C:15]4[S:21][CH:20]=[CH:19][C:16]4=[N:17][CH:18]=[C:13]3[N:12]=2)[CH2:23]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178511080HCID 178511080, compound

Product 1

HCID 178511079HCID 178511079, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-{1-[trans-4-(Cyanomethyl)cyclohexyl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl}azetidine-1-carboxylate (14 mg, 0.031 mmol) was treated with trifluoroacetic acid (1 mL) in methylene chloride (1 mL) at room temperature for 1 h. The mixture was stripped to dryness, diluted with MeOH and purified on prep-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product. LCMS calculated for C19H22N5S (M+H)+: m/z=352.2. Found: 352.0.

Workup

  1. custompurified on prep-HPLC (XBridge C18 column
  2. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-e579f2d44e66431987a7b1ff829d13ac
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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