Diisopropylethylamine → HCID 57635077, compound

HRID 2111444Notes

Reaction equation

HRID 2111444 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[N:14]=[CH:15][C:16]2[N:25]([CH3:26])[C:24](=[O:27])[CH2:23][C@@H:22]3[N:18]([CH2:19][CH2:20][CH2:21]3)[C:17]=2[N:28]=1)[C:6]([OH:8])=O.C(N(C(C)C)C(C)C)C.[NH2:38][CH:39]1[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]1>CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[N:14]=[CH:15][C:16]2[N:25]([CH3:26])[C:24](=[O:27])[CH2:23][C@@H:22]3[N:18]([CH2:19][CH2:20][CH2:21]3)[C:17]=2[N:28]=1)[C:6]([NH:38][CH:39]1[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]1)=[O:8]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 68737897HCID 68737897, compound

Product 1

HCID 57635077HCID 57635077, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a mixture of 3-methoxy-4-((R)-6-methyl-5-oxo-2,3,3a,4,5,6-hexahydro-1H-6,8,10,10b-tetraaza-benzo[e]azulen-9-ylamino)-benzoic acid (I-102a), 0.32 mL (0.0018 mole) of ethyldiisopropylamine and 0.082 g (0.00072 mole) of 4-amino-1-methyl-piperidine in 3.0 mL of dimethylformamide was added 0.31 g (0.00072 mole) of 1-(di-1-pyrrolidinylmethylene)-1H-benzotriazolium 3-oxide hexafluorophosphate. The mixture was stirred at room temperature for 3 hours, then diluted with saturated sodium carbonate. The mixture was extracted with ethyl acetate three times. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by silica gel chromatography, eluting with dichloromethane-methanol (100:0-60:40) gave 0.060 g of 3-methoxy-4-((R)-6-methyl-5-oxo-2,3,3a,4,5,6-hexahydro-1H-6,8,10,10b-tetraaza-benzo[e]azulen-9-ylamino)-N-(1-methyl-piperidin-4-yl)-benzamide (I-102).

Workup

  1. extractionThe mixture was extracted with ethyl acetate three times
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by silica gel chromatography
  6. washeluting with dichloromethane-methanol (100:0-60:40)

Sources & evidence

ORD record
ord-cb70ef25331a45268ae9aa1bf749eff3
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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