1,2-Dichloroethane → HCID 54179784, compound

HRID 1740589Notes

Reaction equation

HRID 1740589 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](O)=[O:17])=[C:11]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:25]1[CH:26]=[CH:27][C:28]2N(O)N=[N:31][C:29]=2[CH:30]=1.[CH2:35](Cl)CCl.[CH3:39][CH2:40][N:41](C(C)C)[CH:42](C)[CH3:43].C[N:49]([CH:51]=[O:52])C>>[F:22][C:21]([F:24])([F:23])[CH2:20][O:19][C:11]1[CH:10]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:14]=[CH:13][C:12]=1[CH2:15][C:16]([N:41]1[CH2:42][CH2:43][N:31]([C:29]2[CH:30]=[CH:25][CH:26]=[CH:27][C:28]=2[CH3:35])[CH2:39][CH:40]1[C:51](=[O:52])[NH2:49])=[O:17]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 543655024-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-(2,2,2-trifluoroethoxy)benzeneacetic acid

Product 1

HCID 54179784HCID 54179784, compound

Procedure

To a stirred solution of 4-(tert-butyloxycarbonylmino)-2-(2,2,2-trifluoroethoxy)phenylacetic acid (0.20 g, 0.59 mmol) from Step 9 above in DMF (10 mL) was added 2-carbamoyl-4-(2-methylhenyl)piperazine (0.13 g, 0.59 mmol) from Step 4 of Example 1, HOBT (0.09 g, 0.6 mmol), EDC (0.15 g, 0.90 mmol), and DIEA (0.15 mL, 0.90 mmol). The solution was stirred at ambient temperature for 14 h during which time a precipitate had formed. The mixture was cooled, filtered, and the solid was washed with EtOAc and dried under reduced pressure to give 1-(2-(2,2,2-trifluoroethoxy)-4-(tert-butyloxycarbonylamino)phenylacetyl)-2-carbamoyl-4-(2-methylphenyl)-piperazine as an amorphous solid (HPLC retention time=10.0 min (method A); TLC Rf =0.40 (3:1 EtOAc:hexanes).

Workup

  1. customhad formed
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe solid was washed with EtOAc
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-029e96f47d6d4657b2370c0a960cc701
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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