1-Hydroxybenzotriazole → HCID 58012226, compound

HRID 660965Notes

Reaction equation

HRID 660965 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:9](=[O:16])[N:10]([CH2:12][C:13](O)=[O:14])[CH:11]=2)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[F:47][C:48]([F:60])([F:59])[C:49]1[CH:50]=[C:51]([C:55]([NH2:58])([CH3:57])[CH3:56])[CH:52]=[CH:53][CH:54]=1>CN(C=O)C.O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:9](=[O:16])[N:10]([CH2:12][C:13]([NH:58][C:55]([CH3:57])([C:51]3[CH:52]=[CH:53][CH:54]=[C:49]([C:48]([F:59])([F:60])[F:47])[CH:50]=3)[CH3:56])=[O:14])[CH:11]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 194252732-[3-(Trifluoromethyl)phenyl]propan-2-amineHCID 58011727HCID 58011727, compound

Product 1

HCID 58012226HCID 58012226, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

45 mg (0.123 mmol) of [4-(5-chloro-2-thienyl)-3-(2-fluorobenzyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid from Example 238A, 20 mg (0.147 mmol) of HOBt and 31 mg (0.159 mmol) of EDC hydrochloride are placed in 1.5 ml of DMF and stirred for 10 mins. Next, 30 mg (0.147 mmol) of 1-methyl-1-[(3-trifluoromethyl)phenyl]ethylamine from Example 1A are added and the mixture is stirred overnight at RT. For the workup, the reaction mixture is stirred with 2 ml of water and extracted twice with 5 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulphate, filtered and concentrated in vacuo. The crude product is purified by preparative HPLC [Method 10]. 50 mg (74% of theory) of the target compound are thus obtained.

Workup

  1. stirringthe mixture is stirred overnight at RT
  2. extractionextracted twice with 5 ml of ethyl acetate each time
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by preparative HPLC [Method 10]
  7. custom50 mg (74% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-d8edeba3787940029f12c38262740b23
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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