Cyanoacetamide → HCID 178453633, compound

HRID 712137Notes

Reaction equation

HRID 712137 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][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[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:1]([CH2:3][C:4]1[N:29]([C@H:30]2[CH2:31][CH2:32][C@H:33]([CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:41])([CH3:43])[CH3:42])[CH2:34][CH2:35]2)[C:21]2=[C:22]3[S:28][CH:27]=[CH:26][C:23]3=[N:24][CH:25]=[C:20]2[N:19]=1)#[N:2]

Participants

6

Reactant 3

HCID 7898CyanoacetamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 178453639HCID 178453639, compound

Product 1

HCID 178453633HCID 178453633, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-Cyanoacetamide (120 mg, 1.5 mmol) and triethyloxonium tetrafluoroborate (270 mg, 1.4 mmol) in THF (1.1 mL) was stirred at room temperature for 2 h. The solvent was removed and the residue dissolved in ethanol (0.5 mL) and added to a suspension of tert-butyl ({trans-4-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}methyl)carbamate (150 mg, 0.40 mmol) in ethanol (1.7 mL). The mixture was stirred at 85° C. for 2 h. The solid was filtered and the filtrate was concentrated and purified on flash chromatography (0-10% methanol/dichloromethane) to give the desired product (0.12 g, 71%). LCMS calculated for C22H28N5O2S (M+H)+: m/z=426.2. Found: 426.0.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in ethanol (0.5 mL)
  3. stirringThe mixture was stirred at 85° C. for 2 h
  4. filtrationThe solid was filtered
  5. concentrationthe filtrate was concentrated
  6. custompurified on flash chromatography (0-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-9202a4dd32bd4126839856b2594f83ec
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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