Acetic Acid → HCID 470669, compound

HRID 724968Notes

Reaction equation

HRID 724968 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH:19]=O)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.C([BH3-])#N.[Na+].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(=O)C>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19][NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 5003444Sodium cyanoborohydrideHCID 10639163HCID 10639163, compound

Product 1

HCID 470669HCID 470669, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 2-chloro-5,11-dihydro-11-ethyl-8-formyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.50 g, 0.16 mmol) was dissolved/suspended in methanol (2 mL) and treated with sodium cyanoborohydride (0.030 g, 0.47 mmol) followed by aniline (0.043 mL, 4.7 mmol). The mixture was stirred for 5 minutes then acetic acid (0.020 mL, 0.35 mmol) was added. After an additional 3 hours at room temperature the mixture was made alkaline with 15% sodium hydroxide and the white suspension was extracted with dichloromethane (3×10 mL). The combined organics were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography then chromatotron (hexane to 1:1 hexanes/ethyl acetate gradient) to give the title compound (0.031 g, 50%), m.p. 79°-80° C.

Workup

  1. waitAfter an additional 3 hours at room temperature the mixture was made
  2. extractionalkaline with 15% sodium hydroxide and the white suspension was extracted with dichloromethane (3×10 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-523443f5d5f148f7885c6bc8f87b2b1f
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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