Diisopropylethylamine → HCID 21868525, compound

HRID 857437Notes

Reaction equation

HRID 857437 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4]([Cl:10])=[N:5][C:6](Cl)=[N:7][CH:8]=1.[NH2:13][C:14]1[CH:15]=[C:16]2[CH2:22][C:21](=[O:23])[NH:20][C:17]2=[N:18][CH:19]=1.C(N(C(C)C)CC)(C)C.N1C2C(=CC=CC=2)CC1=O.FC(C1N=CC=CN=1)(F)F>[Cl-].[Zn+2].[Cl-].C(O)(C)(C)C.ClCCCl.ClCCCl.C(O)(C)(C)C>[Cl:10][C:4]1[C:3]([C:2]([F:12])([F:11])[F:1])=[CH:8][N:7]=[C:6]([NH:13][C:14]2[CH:15]=[C:16]3[CH2:22][C:21](=[O:23])[NH:20][C:17]3=[N:18][CH:19]=2)[N:5]=1

Participants

10

Reactant 5

HCID 81531DiisopropylethylamineHCID 321710OxindoleHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 140077562-(Trifluoromethyl)pyrimidineHCID 21868704HCID 21868704, compound

Product 1

HCID 21868525HCID 21868525, compoundYield 13%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalyst2×HCID 111,2-DichloroethaneSolventHCID 6386tert-ButanolSolventHCID 21868497Tert-butyl alcohol 1,2-dichloroethaneSolvent

Procedure

211 mg (0.972 mmol) 5-trifluoromethyl-2,4-dichloropyrimidine was taken into 1.00 mL 1:1 tert-butanol:1,2-dichloroethane mixture. To this was added 972 mL (0.972 mmol) zinc chloride solution. 145 mg (0.972 mmol) 5-Amino-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one was taken into 500 mL tert-butanol/1,2-dichloroethane mix with 169 mL (0.972 mmol) diisopropylethylamine and 2.92 mL (2.92 mmol) zinc chloride solution. Allowed both solutions stir at ambient temperature for thirty minutes. The oxindole-bearing solution was slowly added drop-wise to the solution containing the trifluoromethylpyrimidine. Allowed the combined solutions to stir at ambient temperature for sixteen hours. The volatiles from the reaction mixture were removed under reduced pressure. The resulting glass was taken up into 10% methanol in dichloromethane and washed thoroughly with 1 N sodium hydroxide. Organic layer was dried over magnesium sulfate and evaporated under reduced pressure to give a yellow solid. The titled compound was obtained through purification of this yellow solid over silica (97.8:2:0.2 CHCl3:CH3OH:NH4OH) as a yellow solid in a 13% yield (43 mg, 0.130 mmol). APCI m/z 330.0/331.9 (MH+), 1H NMR (D6-DMSO) δ 10.96 (s, 1 H), 10.57 (s, 1 H), 8.74 (s, 1 H), 8.23 (s, 1 H), 7.85 (s, 1 H), 3.56 (s, 2 H) ppm.

Workup

  1. stirringAllowed the combined solutions to stir at ambient temperature for sixteen hours
  2. customThe volatiles from the reaction mixture were removed under reduced pressure
  3. washwashed thoroughly with 1 N sodium hydroxide
  4. dry with materialOrganic layer was dried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto give a yellow solid

Sources & evidence

ORD record
ord-286c87b54d684172a8b1a891c4785bc0
Source dataset
uspto-grants-2006_12
Patent number
US07145008B2

Reaction notes

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