N,N-Diethylaniline → HCID 86732430, compound

HRID 1776399Notes

Reaction equation

HRID 1776399 reaction equation
[C:1]([C:4]1[C:5]([O-])=[N:6][C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[N:11]=2)=[N:8][CH:9]=1)(=O)[NH2:2].[Na+].P(Cl)(Cl)([Cl:31])=O.C(N(CC)C1C=CC=CC=1)C>>[Cl:31][C:5]1[C:4]([C:1]#[N:2])=[CH:9][N:8]=[C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[N:11]=2)[N:6]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 86732428HCID 86732428, compound

Product 1

HCID 86732430HCID 86732430, compound

Conditions

Temperature
90 °C

Procedure

88 mg of sodium 5-carbamoyl-2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]pyrimidin-4-olate (1-13-1, 0.228 mmol, 1 eq.) were suspended in 0.915 ml of phosphoric trichloride (9.82 mmol, 43 eq.) and 69 μl of N,N-diethylaniline (0.457 mmol, 2 eq.). The suspension was stirred at 90° C. bath temperature for 24 hours and then dropped to an ice cooled saturated aqueous sodium hydrogen carbonate solution. The resulting suspension was filtered off and dried in vacuo to yield 82 mg (0.21 mmol, 93.77%) of the analytically pure target compound.

Workup

  1. filtrationThe resulting suspension was filtered off
  2. customdried in vacuo
  3. customto yield 82 mg (0.21 mmol, 93.77%) of the analytically pure target compound

Sources & evidence

ORD record
ord-0e11e361cfc44b928c108c71cc835eec
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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