1,2-Dichloroethane → HCID 178522670, compound

HRID 1669827Notes

Reaction equation

HRID 1669827 reaction equation
[CH:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[N:9]([CH2:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.O.[NH2:48][C:49]1[NH:53][N:52]=[N:51][N:50]=1>CN(C=O)C.O>[CH:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]([F:21])([F:20])[F:22])=[CH:16][CH:17]=3)[N:9]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([C:28]([NH:48][C:49]4[NH:53][N:52]=[N:51][N:50]=4)=[O:30])=[CH:31][CH:32]=3)[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 533232474-((3-cyclohexyl-5-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-1-yl)methyl)benzoic acidHCID 178509300HCID 178509300, compound

Product 1

HCID 178522670HCID 178522670, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 70 mg product from Step A above, 38.1 mg EDC, 26.9 mg HOBt in 1 mL DMF was stirred at room temperature for 30 minutes. 5-Aminotetrazole monohydrate (20.5 mg) was added and the mixture stirred for additional 16 hours. Precipitate the product by adding 1 mL water to the reaction mixture. Collect the product by filtration, wash it with 1:1 DMF and water, water, and MeCN, and dry to give the title compound as a white solid. 1H NMR (CD3OD, 600 MHz) δ 7.92 (d, J=8.4 Hz, 2H), 7.42˜7.45 (m, 2H), 7.30 (d, J=8.2 Hz, 2H), 7.08 (d, J=8.4 Hz, 2H), 6.32 (s, 1H), 5.42 (s, 2H), 2.67 (tt, J=3.5 & 11.5 Hz, 1H), 1.97˜2.01 (m, 2H), 1.81˜1.85 (m, 2H), 1.72˜1.76 (m, 1H), 1.46˜1.53 (m, 2H), 1.38˜1.47 (m, 2H), 1.26˜1.35 (m, 1H). LC-MS: 2.30 min. (M+H=512.3).

Workup

  1. customCollect the product
  2. filtrationby filtration
  3. washwash it with 1:1 DMF and water, water, and MeCN
  4. customdry

Sources & evidence

ORD record
ord-acb8c5497d8f4e54a7ae14caf3b895b4
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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