Carbonic acid-guanidine (1:1) → HCID 11382785, compound

HRID 1592070Notes

Reaction equation

HRID 1592070 reaction equation
N[C:2]1[C:10]2[C:5](=[N:6][C:7]([N:14]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]3)=[CH:8][C:9]=2[CH2:11][CH2:12][CH3:13])[S:4][C:3]=1[C:21]#[N:22].C(=O)(O)O.[NH2:27][C:28]([NH2:30])=[NH:29]>>[NH2:29][C:28]1[N:30]=[C:21]([NH2:22])[C:3]2[S:4][C:5]3[N:6]=[C:7]([N:14]4[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]4)[CH:8]=[C:9]([CH2:11][CH2:12][CH3:13])[C:10]=3[C:2]=2[N:27]=1

Participants

3

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 58997600HCID 58997600, compound

Product 1

HCID 11382785HCID 11382785, compoundYield 33%

Procedure

3-Amino-6-(4-hydroxy-piperidin-1-yl)-4-propyl-thieno[2,3-b]pyridine-2-carbonitrile (316 mg, 1.00 mol) (see Example 2) and guanidine carbonate (360 mg, 2 mmol) was mixed in a test tube. The mixture was heated to a melt for 15 min until the gas evolution stopped. After cooling to room temperature, the mixture purified by flash chromatography (35 g silica gel cartridge, 10% MeOH in dichloromethane, 30 mL/min for 15 min, Rf=0.25) to give the title compound as a yellow solid (120 mg, 33%).

Workup

  1. temperatureThe mixture was heated to a melt for 15 min until the gas evolution
  2. customthe mixture purified by flash chromatography (35 g silica gel cartridge, 10% MeOH in dichloromethane, 30 mL/min for 15 min, Rf=0.25)

Sources & evidence

ORD record
ord-ad9d68f975d3436097a09ceb90bcede6
Source dataset
uspto-grants-2007_11
Patent number
US07291733B2

Reaction notes

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