1,2-Dichloroethane → HCID 89783377, compound

HRID 58097Notes

Reaction equation

HRID 58097 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]2[C:13]=1[CH:14]=[N:15][NH:16]2)[C:6]([OH:8])=O.C(Cl)CCl.C1C=CC2N(O)N=[N:35][C:33]=2C=1.CN.CCN(C(C)C)C(C)C>CO.CC(N(C)C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]1[CH:20]=[C:19]([C:21]([F:23])([F:24])[F:22])[CH:18]=[C:17]2[C:13]=1[CH:14]=[N:15][NH:16]2)[C:6]([NH:35][CH3:33])=[O:8]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 89783061HCID 89783061, compound

Product 1

HCID 89783377HCID 89783377, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

A 20 mL vial was charged with 3-methoxy-4-(6-(trifluoromethyl)-1H-indazol-4-yl)benzoic acid (0.04 g, 0.119 mmol), EDC (0.034 g, 0.178 mmol), HOBt (0.027 g, 0.178 mmol), methanamine (0.178 mL, 0.357 mmol), DMA (1 mL), and DIPEA (0.062 mL, 0.357 mmol). The vial was capped and the reaction mixture was stirred at room temperature for 2 days. The reaction mixture was subsequently diluted with methanol and purified via preparative HPLC, eluting with a gradient of 35-55% ACN (containing 0.1% formic acid) in H2O (containing 0.1% formic acid). The product fractions were collected and dried in vacuo to give a formic acid salt of the title compound as a white solid (23.6 mg, 56.8%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.84 (d, J=4.29 Hz, 3H), 3.83 (s, 3H), 7.37 (s, 1H), 7.49-7.56 (m, 1H), 7.56-7.62 (m, 1H), 7.65 (s, 1H), 7.94 (s, 1H), 7.97 (s, 1H), 8.60 (d, J=4.55 Hz, 1H), 13.61 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C17H14F3N3O2, 350.1. found 350.2.

Workup

  1. customThe vial was capped
  2. custompurified via preparative HPLC
  3. washeluting with a gradient of 35-55% ACN (containing 0.1% formic acid) in H2O (containing 0.1% formic acid)
  4. customThe product fractions were collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bb2c63136765489bb755e3435d46fe3e
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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