4-Chloro-2-fluorobenzoyl chloride → HCID 21905770, compound

HRID 1246791

Reaction equation

HRID 1246791 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:3]=1[NH2:16].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[C:20]([F:27])[CH:19]=1>N1C=CC=CC=1.C(O)C>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:16][C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[NH:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)=[O:23])=[C:20]([F:27])[CH:19]=1

Participants

5

Reactant 2

HCID 27736014-Chloro-2-fluorobenzoyl chlorideHCID 167263116-Chloro-N~4~-(4-chlorophenyl)pyrimidine-4,5-diamine

Product 1

HCID 21905770HCID 21905770, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

6-Chloro-N4-(4-chlorophenyl)-pyrimidine-4,5-diamine I-(1A-1)a (6.6 g, 26 mmol) in pyridine (30 ml) was cooled to 0° C. and to it was added 4-chloro-2-fluorobenzoyl chloride (5 g, 26 mmol). The reaction was then allowed to warm to ambient temperature overnight. The heterogeneous reaction was diluted with ethanol (50 ml) and the resulting solid collected by filtration. The solids were slurried in toluene, which was then removed under reduced pressure to remove residual ethanol. The solid was slurried in diethyl ether and then collected by filtration to give I-(7A-91)a (8.3 g, 78%): +ACPI MS (M+1) 409.0; 1H NMR (400 MHz, CD3OD) δ 10.60 (s, 1H), 10.10 (s, 1H), 9.19 (s, 1H), 8.74 (t, J=8.1 Hz, 1H), 8.46–8.40 (m, 3H), 8.28 (dd, J=8.7, 2.1 Hz, 1H), 8.20 (d, J=8.7 Hz, 2H).

Workup

  1. customThe heterogeneous reaction
  2. filtrationthe resulting solid collected by filtration
  3. customwhich was then removed under reduced pressure
  4. customto remove residual ethanol
  5. filtrationcollected by filtration
  6. customto give I-(7A-91)a (8.3 g, 78%)

Sources & evidence

ORD record
ord-1800146ac7c349e69101ea3ed85714e4
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Linked notes

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