Guanidine → HCID 20729541, compound

HRID 852301Notes

Reaction equation

HRID 852301 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-7e556ac7efbc4216850695948e8b9e4d
Source dataset
uspto-grants-2007_08
Patent number
US07253187B2

Reaction notes

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