Isopropylamine → HCID 10207923, compound

HRID 896696Notes

Reaction equation

HRID 896696 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([CH:20]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=4)[C:21](O)=[O:22])[CH:17]=[CH:18][CH:19]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.[CH:46]([NH2:49])([CH3:48])[CH3:47]>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[CH:46]([NH:49][C:21](=[O:22])[CH:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:12]2[CH:13]=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH:15]=1)[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1)([CH3:48])[CH3:47]

Participants

8

Reactant 3

HCID 6363IsopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10277075HCID 10277075, compound

Product 1

HCID 10207923HCID 10207923, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of Example 93 (100 mg, 0.21 mmol) in CH2Cl2 (2 mL) was added DMAP (26 mg, 0.21 mmol), EDCI (45 mg, 0.23 mmol), then isopropyl amine (1 mL, 12 mmol). The resulting reaction mixture was stirred 18 h at 21° C., then diluted with a sodium bicarbonate solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 80:20 to 20:80) provided the title compound.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate, 80:20 to 20:80)

Sources & evidence

ORD record
ord-f0c763314cb446c7803187afb7091318
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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