Cyclopropanemethanamine → HCID 68523189, compound

HRID 1989803Notes

Reaction equation

HRID 1989803 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(OC(N(C)C)=[N+](C)C)[C:12]2[CH:13]=[CH:14][CH:15]=CC=2N=N1.[NH2:25][C:26]1[N:34]=[C:33]([C:35](O)=[O:36])[N:32]=[C:31]2[C:27]=1[NH:28][CH:29]([O:45][CH3:46])[N:30]2[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(C(C)C)CC)(C)C.NCC1CC1>CC(N(C)C)=O>[NH2:25][C:26]1[N:34]=[C:33]([C:35]([NH:8][CH2:12][CH:13]2[CH2:15][CH2:14]2)=[O:36])[N:32]=[C:31]2[C:27]=1[NH:28][CH:29]([O:45][CH3:46])[N:30]2[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68526899HCID 68526899, compound

Product 1

HCID 68523189HCID 68523189, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

O-benzotriazol-1-yl-tetramethyluronium hexafluorophosphate (89 mg, 0.235 mmol) was added to a solution of 6-amino-9-benzyl-8-methoxy-8,9-dihydro-7H-purine-2-carboxylic acid (Example 246) (64 mg, 0.214 mmol) and diisopropylethylamine (75 μl, 0.428 mmol) in dimethylacetamide (0.5 ml) and the reaction mixture stirred at room temperature for 1 hour. Aminomethylcyclopropane (28 μl, 0.321 mmol) was added and the reaction mixture stirred at room temperature for a further 20 hours. The reaction mixture was concentrated in vacuo and water added. The resultant precipitate was collected by filtration, azeotroped with toluene and triturated with methanol to yield the title compound.

Workup

  1. stirringthe reaction mixture stirred at room temperature for a further 20 hours
  2. concentrationThe reaction mixture was concentrated in vacuo and water
  3. additionadded
  4. filtrationThe resultant precipitate was collected by filtration
  5. customazeotroped with toluene
  6. customtriturated with methanol

Sources & evidence

ORD record
ord-648168c90bad488c9f26f74af3f26a24
Source dataset
uspto-grants-2010_01
Patent number
US07642350B2

Reaction notes

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