Methylamine → HCID 58980975, compound

HRID 1181800Notes

Reaction equation

HRID 1181800 reaction equation
[CH2:1]([N:3](CC)CC)C.C(OC(Cl)=O)C(C)C.[CH2:16]([N:20]1[C:25]2=[N:26][N:27]([CH2:38][C:39]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH:42]=[CH:41][CH:40]=3)[C:28]([C:29]3[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=3)[C:32](O)=[O:33])=[C:24]2[C:23](=[O:49])[N:22]([CH3:50])[C:21]1=[O:51])[CH:17]([CH3:19])[CH3:18].CN>C1COCC1.O>[CH2:16]([N:20]1[C:25]2=[N:26][N:27]([CH2:38][C:39]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH:42]=[CH:41][CH:40]=3)[C:28]([C:29]3[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=3)[C:32]([NH:3][CH3:1])=[O:33])=[C:24]2[C:23](=[O:49])[N:22]([CH3:50])[C:21]1=[O:51])[CH:17]([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 58980927HCID 58980927, compound

Product 1

HCID 58980975HCID 58980975, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.04 mL) followed by isobutylchloroformate (0.033 g) were added to a solution of 3-[7-isobutyl-5-methyl-2-(1-naphthylmethyl)-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]benzoic acid (0.08 g) in THF (1 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour. Methylamine (2M, 2 mL) was added and the mixture was stirred at 0° C. for 1 h, then at room temperature for 2 h. Reaction was diluted with water (10 mL) and extracted with dichloromethane (2×10 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified on preparative HPLC to give the title compound (0.027 g).

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 h
  2. waitat room temperature for 2 h
  3. customReaction
  4. extractionextracted with dichloromethane (2×10 mL)
  5. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified on preparative HPLC

Sources & evidence

ORD record
ord-8de4373798f44b81b3726083ad988dc0
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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