Dichloromethane → Ammonium Hydroxide

HRID 1445444Notes

Reaction equation

HRID 1445444 reaction equation
C([O:5]C([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:14]=1[C:15]([NH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[NH:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=[O:16])=O)(C)(C)C.FC(F)(F)C(O)=O.ClCCl.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:14]=1[C:15]([NH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[NH:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=[O:16].[OH-:5].[NH4+:8]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 69492866N4-[2-(3-tert-Butoxycarbonylaminopropoxy)-4-methoxybenzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine

Product 2

HCID 14923Ammonium HydroxideHCID 69491278N3-(4-methoxybenzoyl)-N4-[4-methoxy-2-(3-aminopropoxy)benzoyl]-3,4-pyridinediamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N4-[2-(3-tert-Butoxycarbonylaminopropoxy)-4-methoxybenzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine (1.0 g, 1.8 mmol) was dissolved in ice cold dichloromethane (20 mL). Trifluoroacetic acid (10 mL) was then added and the mixture stirred on ice for 1 hour. Modest gas evolution was observed. The mixture was concentrated in vacuo. The oily residue was redissolved in 1:1 toluene:dichloromethane (20 mL) and reconcentrated to give a brown oil. The brown oil was vigorously stirred overnight with a mixture of dichloromethane (50 mL) and potassium carbonate (3.4 g) in water (50 mL). The organic layer was washed with brine, dried and concentrated to give partially pure N4-[2-(3-aminopropoxy)-4-methoxybenzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine as a brittle brown foam (0.74 g, 90%, about 50%-60% pure via TLC (9:1 dichloromethane:MeOH w/few drops of ammonium hydroxide). This material was used without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe oily residue was redissolved in 1:1 toluene
  3. customto give a brown oil
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6505f9140f1244b08e1c26e9539dbcce
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

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