Water → HCID 58012101, compound

HRID 660926Notes

Reaction equation

HRID 660926 reaction equation
[CH:1]1([N:4]2[CH:8]=[N:7][NH:6][C:5]2(CC(O)=O)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[CH2:3][CH2:2]1.[C:20]1([CH2:26][CH2:27][NH2:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1C=CC2N([OH:38])N=NC=2C=1.CCN=C=NC[CH2:45][CH2:46]N(C)C.Cl.[OH2:51]>CN(C)C=O>[CH:1]1([N:4]2[C:8](=[O:51])[N:7]([CH2:45][C:46]([NH:28][CH2:27][CH2:26][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:38])[N:6]=[C:5]2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 962WaterHCID 1001PhenethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69070067HCID 69070067, compound

Product 1

HCID 58012101HCID 58012101, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40.0 mg (0.144 mmol) of [4-cyclopropyl-3-(2-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-yl]-acetic acid from Example 92A, 19.2 mg (0.159 mmol) of 2-phenylethylamine and 23.4 mg (0.173 mmol) of HOBt are placed in 2 ml of dimethylformamide and treated with 36.0 mg (0.188 mmol) of EDC hydrochloride. This is stirred overnight at room temperature, then diluted with 10 ml of water and extracted with ethyl acetate. After evaporation of the organic phase, the crude product is purified by preparative HPLC [Method 9]. 32.0 mg (58% of theory) of the target compound are thus obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter evaporation of the organic phase
  3. customthe crude product is purified by preparative HPLC [Method 9]
  4. custom32.0 mg (58% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-526fdc5f707f48e5b836239ca8b0e5e8
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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