Cyclopropylamine → HCID 67349865, compound

HRID 1672858Notes

Reaction equation

HRID 1672858 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[N:13]([C:17]3[CH:18]=[C:19]([C:23]4[O:27][C:26](=[O:28])[N:25]([CH3:29])[N:24]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:12][C@H:11]3[N:7]([CH2:8][CH2:9][CH2:10]3)[C:6]=2[N:5]=[C:4]([S:30][CH3:31])[N:3]=1.[CH:32]1([NH2:35])[CH2:34][CH2:33]1>C1COCC1>[CH:32]1([NH:35][C:2]2[C:15]3[C:14](=[O:16])[N:13]([C:17]4[CH:18]=[C:19]([C:23]5[O:27][C:26](=[O:28])[N:25]([CH3:29])[N:24]=5)[CH:20]=[CH:21][CH:22]=4)[CH2:12][C@H:11]4[N:7]([CH2:8][CH2:9][CH2:10]4)[C:6]=3[N:5]=[C:4]([S:30][CH3:31])[N:3]=2)[CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 86643709HCID 86643709, compound

Product 1

HCID 67349865HCID 67349865, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-5-[3-(7-Chloro-9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-3-methyl-1,3,4-oxadiazol-2(3H)-one (30.0 mg, 0.0654 mmol) obtained in Step 8 of Example 156 was dissolved in THF (3 mL), and the mixture was stirred at room temperature for 17 hours after adding cyclopropylamine (0.023 mL, 0.327 mmol). The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give (S)-5-[3-(7-cyclopropylamino-9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-3-methyl-1,3,4-oxadiazol-2 (3H)-one.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e9670fc745434259abdacd00b7397202
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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