Guanidine → HCID 20729541, compound

HRID 351614Notes

Reaction equation

HRID 351614 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:5][NH:6][C:7]([C:9]1[NH:10][CH:11]=[C:12]([C:14](=O)[CH2:15][CH3:16])[CH:13]=1)=[O:8].[CH:22](OC(C)(C)C)(N(C)C)N(C)C.[NH2:34][C:35]([NH2:37])=[NH:36]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:5][NH:6][C:7]([C:9]1[NH:10][CH:11]=[C:12]([C:14]2[C:15]([CH3:22])=[CH:16][N:34]=[C:35]([NH2:37])[N:36]=2)[CH:13]=1)=[O:8]

Participants

5

Reactant 3

HCID 3520GuanidineHCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 20729568HCID 20729568, compound

Product 1

HCID 20729541HCID 20729541, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 6 (1 equivalent) in THF, at ambient temperature, was added (Me2N)2CHOt-Bu (3 equivalents). After 24 hours, the solvent was evaporated and the crude product was utilized without purification. Step 2: To a solution of the compound formed above at Step 1 (1 equivalent) in ethanol, at ambient temperature, was added guanidine (3 equivalents) and the resulting mixture heated at reflux. After 12 hours, the solvent was evaporated and the crude product purified by preparatory HPLC (reverse phase; 10→90% MeCN in water; 15 minutes) to afford the desired compound III-a-74. HPLC using method B provided Rt of 7.9 minutes. 1H NMR was consistent with expected structure. FIA/MS Obs. M+1/M−1.

Workup

  1. customthe solvent was evaporated
  2. customthe crude product was utilized without purification
  3. customStep 2: To a solution of the compound formed above at Step 1 (1 equivalent) in ethanol, at ambient temperature
  4. temperaturethe resulting mixture heated
  5. temperatureat reflux
  6. waitAfter 12 hours
  7. customthe solvent was evaporated
  8. customthe crude product purified by preparatory HPLC (reverse phase; 10→90% MeCN in water; 15 minutes)

Sources & evidence

ORD record
ord-34ca46a8156c48f898eaad42986ab3d7
Source dataset
uspto-grants-2004_06
Patent number
US06743791B2

Reaction notes

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