Methylamine → HCID 21930384, compound

HRID 1243733Notes

Reaction equation

HRID 1243733 reaction equation
ClC1C=CC(C#N)=C(OC2C=CC=C3C=2CCC3=O)C=1.[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[C:32]([O:38][C:39]2[CH:47]=[CH:46][CH:45]=[C:44]3[C:40]=2[CH2:41][CH2:42][CH:43]3[NH:48][CH3:49])[CH:31]=1.CN.C([BH3-])#N.[Na+].C(O)(=O)/C=C/C(O)=O>CO.C(O)(=O)C>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[C:32]([O:38][C:39]2[CH:47]=[CH:46][CH:45]=[C:44]3[C:40]=2[CH2:41][CH2:42][CH:43]3[NH:48][CH3:49])[CH:31]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 21930421HCID 21930421, compound

Product 1

HCID 21930384HCID 21930384, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

4-Chloro-2-(1-methylaminoindan-4-yloxy)benzonitrile fumarate 4-Chloro-2-(1-oxoindan-4-yloxy)benzonitrile (0.12 g, 0.42 mmol), methylamine (33% in ethanol, 1.0 mL, 8.0 mmol) and sodium cyanoborohydride (100 mg, 0.86 mmol) were stirred at ambient temperature in a solution of glacial acetic acid (1.0 mL) in methanol (30 mL) for 5 days. The solvent was removed in vacuo. The residue was treated with 10% sodium carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was separated and fumaric acid (40 mg, 0.34 mmol) was added. After the solvent was removed in vacuo, the residue was triturated with ethyl acetate overnight, collected by filtration, and dried to give 4-chloro-2-(1-methylaminoindan-4-yloxy)benzonitrile fumarate (111 mg, 63%) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with 10% sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. customThe ethyl acetate layer was separated
  5. customAfter the solvent was removed in vacuo
  6. customthe residue was triturated with ethyl acetate overnight
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-826989b8b7a540f696ba14e4bdb66a36
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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