Triethylamine → HCID 67430447, compound

HRID 45107Notes

Reaction equation

HRID 45107 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([C:28](O)=[O:29])[CH:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.C(Cl)(=O)C(Cl)=O.[C:46]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])(=[O:49])[NH:47][NH2:48]>C(Cl)Cl.CN(C=O)C>[C:51]([O:50][C:46]([NH:47][NH:48][C:28]([C:24]1[CH:23]=[C:22]([O:21][C:17]2[CH:16]=[C:15]3[C:20](=[CH:19][CH:18]=2)[N:12]([C:10](=[O:11])[NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:32])([F:1])[F:31])[CH:4]=2)[CH:13]=[CH:14]3)[CH:27]=[CH:26][N:25]=1)=[O:29])=[O:49])([CH3:54])([CH3:53])[CH3:52]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 70091tert-Butyl carbazateHCID 59394773HCID 59394773, compound

Product 1

HCID 67430447HCID 67430447, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of acid 4-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyridine-2-carboxylic acid, Example 28-A, (0.100 g, 0.226 mmol) in DCM (5 mL) is added Et3N (0.09 mL), DMF (2 drops) and oxalyl chloride (0.17 mL, 0.340 mmol, 2.0 M DCM). After 0.5 h tert-butyl carbazate is added (0.045 g, 0.340 mmol). After 1.5 h the solution is diluted with DCM (10 mL) and then washed with pH 7 buffer (15 mL). The organic layer is then dried (Na2SO4), filtered, and concentrated. The residue is separated via FCC (30-60% EtOAc/heptane) to give N′-{4-[1-(3-Trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyridine-2-carbonyl}-hydrazinecarboxylic acid tert-butyl ester. MS (ESI) m/z 484.3 (M+1).

Workup

  1. washwashed with pH 7 buffer (15 mL)
  2. dry with materialThe organic layer is then dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is separated via FCC (30-60% EtOAc/heptane)

Sources & evidence

ORD record
ord-b2b7a9a761924e349d6d9c796fb70888
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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