1-(Methylamino)adamantane → 5-Benzyl-1,3-dimethyl-1h-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide

HRID 2279643Notes

Reaction equation

HRID 2279643 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.[CH2:28]([C:35]1[N:39]([CH3:40])[N:38]=[C:37]([CH3:41])[C:36]=1[C:42]([OH:44])=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:45]12(NC)[CH2:54][CH:49]3[CH2:50][CH:51]([CH2:53][CH:47]([CH2:48]3)[CH2:46]1)[CH2:52]2.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:45]12([CH2:12][NH:8][C:42]([C:36]3[C:37]([CH3:41])=[N:38][N:39]([CH3:40])[C:35]=3[CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:44])[CH2:46][CH:47]3[CH2:48][CH:49]([CH2:50][CH:51]([CH2:53]3)[CH2:52]1)[CH2:54]2

Participants

8

Reactant 5

HCID 194761-(Methylamino)adamantaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 595799845-Benzyl-1,3-dimethyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 595798435-Benzyl-1,3-dimethyl-1h-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

BOP (44 mg, 0.1 mmol) is added to a solution of 5-benzyl-1,3-dimethyl-1H pyrazole-4-carboxylic acid (20 mg, 0.087 mmol), admantan-1-yl-methylamine (15 mg, 0.09 mmol), HOBt (5 mg) and DIEA (17 μL, 0.1 mmol) in DMF (0.5 mL) at it. The mixture is stirred for 14 h. H2O is added, and the mixture is extracted with EtOAc (3×10 mL). The organic phase is dried. The title compound is obtained by PTLC using 20% EtOAc in hexane. 1H NMR (CDCl3): 7.29-7.21 (m, 3H), 7.12-7.11 (in, 2H), 5.39 (m, 1H), 4.33 (s, 2H), 3.65 (s, 3H), 3.07 (m, 2H), 2.46 (s, 3H), 1.94 (m, 3H), 1.70-1.56 (m, 12H). MS (M+1)=378.22; RT=1.67 min. *IC50.

Workup

  1. extractionthe mixture is extracted with EtOAc (3×10 mL)
  2. customThe organic phase is dried

Sources & evidence

ORD record
ord-5454bb327f74433781030c2e83611519
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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