1-(Methylamino)adamantane → HCID 178434554, compound

HRID 2279615Notes

Reaction equation

HRID 2279615 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2C=CC=CC=2N=N1.[C:28]12(NC)[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2.[CH3:40][C:41]1[C:45]([C:46]([OH:48])=O)=[CH:44][NH:43][N:42]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:28]12([CH2:12][NH:8][C:46]([C:45]3[C:41]([CH3:40])=[N:42][NH:43][CH:44]=3)=[O:48])[CH2:29][CH:30]3[CH2:31][CH:32]([CH2:33][CH:34]([CH2:36]3)[CH2:35]1)[CH2:37]2

Participants

6

Reactant 4

HCID 194761-(Methylamino)adamantaneHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 5576005-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 178434554HCID 178434554, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BOP (3.53 g, 8 mmol) is added to a solution of adamantan-1-yl-methylamine (1.32 g, 8 mmol), 3-methyl-1H-pyrazole-4-carboxylic acid (1 g, 7 mmol) and DIEA (2.6 g, 20 mmol) in DCM (25 mL). The solution is stirred overnight and evaporated, and then partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic layer is washed with brine, dried and evaporated. The residue is triturated with DCM and air-dried to give the title compound.

Workup

  1. customevaporated
  2. custompartitioned between EtOAc and saturated aqueous sodium bicarbonate
  3. washThe organic layer is washed with brine
  4. customdried
  5. customevaporated
  6. customThe residue is triturated with DCM
  7. customair-dried

Sources & evidence

ORD record
ord-a8d360d9c74a4688bf1359ace9e043ce
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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