Cyanoacetamide → HCID 178510884, compound

HRID 712142Notes

Reaction equation

HRID 712142 reaction equation
[C:1]([CH2:3][C:4](N)=O)#[N:2].F[B-](F)(F)F.C([O+](CC)CC)C.[NH2:19][C:20]1[C:21]([NH:29][C@H:30]2[CH2:35][CH2:34][C@H:33]([CH2:36][C:37]#[N:38])[CH2:32][CH2:31]2)=[C:22]2[S:28][CH:27]=[CH:26][C:23]2=[N:24][CH:25]=1>C1COCC1.C(O)C>[C:37]([CH2:36][C@H:33]1[CH2:32][CH2:31][C@H:30]([N:29]2[C:21]3=[C:22]4[S:28][CH:27]=[CH:26][C:23]4=[N:24][CH:25]=[C:20]3[N:19]=[C:4]2[CH2:3][C:1]#[N:2])[CH2:35][CH2:34]1)#[N:38]

Participants

6

Reactant 3

HCID 7898CyanoacetamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 178511084HCID 178511084, compound

Product 1

HCID 178510884HCID 178510884, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-Cyanoacetamide (11 mg, 0.13 mmol) and triethyloxonium tetrafluoroborate (21 mg, 0.11 mmol) in THF (0.13 mL) was stirred at room temperature for 2 h. The solvent was removed and the residue dissolved in ethanol (55 μL) and added to a suspension of {trans-4-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acetonitrile (8.9 mg, 0.031 mmol) in ethanol (0.20 mL). The mixture was stirred at 85° C. for 2 h. The mixture was purified on prep-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 60 mL/min) to give the desired product (2.7 mg, 26%) as TFA salt. LCMS calculated for C18H18N5S (M+H)+: m/z=336.1. Found: 336.0.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in ethanol (55 μL)
  3. stirringThe mixture was stirred at 85° C. for 2 h
  4. customThe mixture was purified on prep-HPLC (XBridge C18 column
  5. washeluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-14b43eb81263463d91e271e28e7587f1
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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