Sodium Carbonate → HCID 68602450, compound

HRID 448916Notes

Reaction equation

HRID 448916 reaction equation
CCN=C=NCCCN(C)C.Cl.[Cl:13][C:14]1[CH:35]=[CH:34][C:17]([C:18]([N:20]([CH3:33])[C:21]2[CH:32]=[CH:31][CH:30]=[CH:29][C:22]=2[O:23][CH2:24][CH2:25][C:26](O)=[O:27])=[O:19])=[CH:16][C:15]=1[C:36]1[CH:37]=[N:38][C:39]([C:44]([F:47])([F:46])[F:45])=[CH:40][C:41]=1[C:42]#[N:43].[C:48]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])(=[O:51])[NH:49][NH2:50].C1C=CC2N(O)N=NC=2C=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.ClCCl>[C:53]([O:52][C:48]([NH:49][NH:50][C:26](=[O:27])[CH2:25][CH2:24][O:23][C:22]1[CH:29]=[CH:30][CH:31]=[CH:32][C:21]=1[N:20]([C:18](=[O:19])[C:17]1[CH:34]=[CH:35][C:14]([Cl:13])=[C:15]([C:36]2[CH:37]=[N:38][C:39]([C:44]([F:45])([F:47])[F:46])=[CH:40][C:41]=2[C:42]#[N:43])[CH:16]=1)[CH3:33])=[O:51])([CH3:56])([CH3:55])[CH3:54]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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

EDCl (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-c4dd244eca6d4c2db18649e851997586
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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