Dichloromethane → HCID 66846503, compound

HRID 252193Notes

Reaction equation

HRID 252193 reaction equation
[NH2:1][C:2]1[C:3]([Cl:20])=[C:4]([C:9]2[C:10]([NH2:19])=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16]N=[CH:14][CH:13]=3)[C:5]([Cl:8])=[CH:6][CH:7]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27].Cl[CH2:35]Cl>CCOC(C)=O>[NH2:19][C:10]1[C:9]([C:4]2[C:3]([Cl:20])=[C:2]([NH:1][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][CH:31]=[C:23]([C:22]([F:33])([F:32])[F:21])[CH:24]=3)[CH:7]=[CH:6][C:5]=2[Cl:8])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:35][CH:16]=2)[N:11]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 59860302HCID 59860302, compound

Product 1

HCID 66846503HCID 66846503, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3-amino-2,6-dichloro-phenyl)-[1,6]naphthyridin-2-ylamine (2.0 g, 6.554 mmol) in the dichloromethane (400.0 mL) is added 3-(trifluoromethyl)benzoyl chloride (4.78 g, 22.94 mmol). After the mixture is stirred for 24 hours at room temperature, it is diluted with EtOAc and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by flash silica gel column eluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (NH3, 2N) (95/5) to give the product as a solid: 1H NMR 400 MHz (CDCl3) δ 8.97 (s, 1H), 8.61 (d, 1H), 8.57 (d, 1H), 8.52 (s, 1H), 8.20 (s, 1H), 8.06 (d, 1H), 7.86 (d, 1H), 7.85 (s, 1H), 7.68 (t, 1H), 7.58 (d, 1H), 7.51 (d, 3H), 5.25 (s, 2H); MS m/z 478.10 (M+1).

Workup

  1. washwashed with saturated K2CO3, brine and water
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customis purified by flash silica gel column
  7. washeluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (NH3, 2N) (95/5)

Sources & evidence

ORD record
ord-728385908b6d4efa92701899b50b2250
Source dataset
uspto-grants-2011_01
Patent number
US07868018B2

Reaction notes

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