Trifluoroacetic acid → HCID 71540875, compound

HRID 1776442Notes

Reaction equation

HRID 1776442 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10][C:11]1[C:12]([NH:38][C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)=[N:13][C:14]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][C:27]3[C:32]([F:33])=[CH:31][C:30]([O:34][CH2:35][CH3:36])=[CH:29][C:28]=3[F:37])[N:18]=2)=[N:15][CH:16]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].ClCCl.C(O)(C)C>ClCCl>[NH2:7][CH2:8][CH2:9][O:10][C:11]1[C:12]([NH:38][C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)=[N:13][C:14]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][C:27]3[C:28]([F:37])=[CH:29][C:30]([O:34][CH2:35][CH3:36])=[CH:31][C:32]=3[F:33])[N:18]=2)=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 21966342Isopropanol methylene chlorideHCID 86732469HCID 86732469, compound

Product 1

HCID 71540875HCID 71540875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

28.6 mg of tert-butyl[2-({2-[1-(4-ethoxy-2,6-difluorobenzyl)-1H-indazol-3-yl]-4-(pyridin-4-ylamino)pyrimidin-5-yl}oxy)ethyl]carbamate (4-23, 0.046 mmol, 1.0 eq.) were dissolved in 2 ml of dry dichloromethane. 0.071 ml of trifluoroacetic acid (0.926 mmol, 20.0 eq.) were added at 0° C. The reaction mixture was stirred over night at room temperature. Then a mixture 2 N sodium carbonate and dichloromethane/isopropanol 4:1 was added and the mixture was stirred for 30 min. The phases were separated and the aqueous layer (slightly brown) was extracted twice with dichloromethane/isopropanol 4:1. The combined organic layers were dried over a magnesium sulfate and concentrated in vacuo. The residue was purified by crystallization from ethylacetate to yield 6.8 mg (0.01 mmol, 27.0%) of the analytically pure target compound.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customThe phases were separated
  3. extractionthe aqueous layer (slightly brown) was extracted twice with dichloromethane/isopropanol 4:1
  4. dry with materialThe combined organic layers were dried over a magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by crystallization from ethylacetate
  7. customto yield 6.8 mg (0.01 mmol, 27.0%) of the analytically pure target compound

Sources & evidence

ORD record
ord-9af0cdfcda6d4a45b0585ea2e172f207
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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