Sodium Carbonate → HCID 68602450, compound

HRID 1485984Notes

Reaction equation

HRID 1485984 reaction equation
CCN=C=NCCCN(C)C.[Cl:12][C:13]1[CH:34]=[CH:33][C:16]([C:17]([N:19]([CH3:32])[C:20]2[CH:31]=[CH:30][CH:29]=[CH:28][C:21]=2[O:22][CH2:23][CH2:24][C:25](O)=[O:26])=[O:18])=[CH:15][C:14]=1[C:35]1[CH:36]=[N:37][C:38]([C:43]([F:46])([F:45])[F:44])=[CH:39][C:40]=1[C:41]#[N:42].[C:47]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])(=[O:50])[NH:48][NH2:49].C1C=CC2N(O)N=NC=2C=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.ClCCl>[C:52]([O:51][C:47]([NH:48][NH:49][C:25](=[O:26])[CH2:24][CH2:23][O:22][C:21]1[CH:28]=[CH:29][CH:30]=[CH:31][C:20]=1[N:19]([C:17](=[O:18])[C:16]1[CH:33]=[CH:34][C:13]([Cl:12])=[C:14]([C:35]2[CH:36]=[N:37][C:38]([C:43]([F:44])([F:46])[F:45])=[CH:39][C:40]=2[C:41]#[N:42])[CH:15]=1)[CH3:32])=[O:50])([CH3:55])([CH3:54])[CH3:53]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 251587413-(2-{[4-Chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionic acid

Product 1

HCID 68602450HCID 68602450, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

EDCI (19.9 mg, 0.104 mmol) was added to a solution of 3-(2-{[4-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionic acid 11-4 (36.3 mg, 0.069 mmol), t-butyl carbazate (13.7 mg, 0.104 mmol), HOBt (14.0 mg, 0.104 mmol) and Na2CO3 (8.7 mg, 0.104 mmol) in a mixture of DMF (1 mL) and dichloromethane (4 mL). The mixture was stirred at room temperature for approximately 16 hrs and was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, washed with water and brine, and was dried over MgSO4. The organic filtrate was evaporated and purified by prep. TLC plate eluted with hexane and ethyl acetate (1/1) to yield N′-[3-(2-{[4-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionyl]-hydrazinecarboxylic acid tert-butyl ester (40.1 mg, 94%). MS [M+H]+: 619.0; tR=2.40 min. (method 1)

Workup

  1. customwas partitioned between ethyl acetate and water
  2. customThe ethyl acetate layer was separated
  3. washwashed with water and brine
  4. dry with materialwas dried over MgSO4
  5. customThe organic filtrate was evaporated
  6. custompurified by prep
  7. washTLC plate eluted with hexane and ethyl acetate (1/1)

Sources & evidence

ORD record
ord-4706f02c72344e95b253ab610fba9283
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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