Sulfuric acid magnesium salt (1:1) → HCID 44380222, compound

HRID 1275047Notes

Reaction equation

HRID 1275047 reaction equation
[NH2:1][CH2:2][C@H:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([CH3:25])([CH3:24])[C:15]([N:17]3[CH:21]4[CH2:22][CH2:23][CH:18]3[CH2:19][CH2:20]4)=[O:16])[CH:12]=2)[NH:7][C:6]=1[C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=1)[CH3:4].S([O-])([O-])(=O)=O.[Mg+2].[N:40]1[CH:45]=[CH:44][N:43]=[C:42]2[N:46]=[CH:47][C:48]([CH2:50][CH2:51][CH:52]=O)=[CH:49][C:41]=12.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[OH-:16].[NH4+:1].[CH:21]12[N:17]([C:15](=[O:16])[C:14]([C:11]3[CH:12]=[C:13]4[C:8](=[CH:9][CH:10]=3)[NH:7][C:6]([C:26]3[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=3)=[C:5]4[C@H:3]([CH3:4])[CH2:2][NH:1][CH2:52][CH2:51][CH2:50][C:48]3[CH:47]=[N:46][C:42]4=[N:43][CH:44]=[CH:45][N:40]=[C:41]4[CH:49]=3)([CH3:25])[CH3:24])[CH:18]([CH2:23][CH2:22]1)[CH2:19][CH2:20]2

Participants

8

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 12149997HCID 12149997, compoundHCID 22118869HCID 22118869, compound

Product 2

HCID 14923Ammonium HydroxideHCID 44380222HCID 44380222, compoundYield 14.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of (S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-azabicyclo[2.2.1]hept-7-yl)-2methylpropan-1-one (120 mg in 8 mL dry chloroform) at 0° C. was added 194 mg magnesium sulfate followed by 51 mg 3-pyrido[2,3-b]pyrazin-7-yl-propionaldehyde and the mixture stirred at low temperature. After 1 hour, a solution of sodium cyanoborohydride (34 mg in 0.7 mL methanol) was added followed by 0.25 mL of a solution of acetic acid in methanol (1:9) and the reaction allowed to warm to room temperature. After 1 hour, the reaction was quenched by the addition of saturated sodium bicarbonate and the mixture extracted with ethyl acetate. The organic portion was washed with saturated aqueous sodium bicarbonate and then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate; then methylene chloride:methanol:ammonium hydroxide, 94:5:1) gave the title compound (12 mg).

Workup

  1. waitAfter 1 hour
  2. customthe reaction was quenched by the addition of saturated sodium bicarbonate
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe organic portion was washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-6415f6f8354544c39e4656bae6be5ed1
Source dataset
uspto-grants-2000_12
Patent number
US06159975

Reaction notes

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