Diisopropylamine → HCID 10238158, compound

HRID 10371Notes

Reaction equation

HRID 10371 reaction equation
[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]([S:8]([NH:11][C:12]2[S:13][C:14]([CH2:17][C:18]([OH:20])=O)=[CH:15][N:16]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[CH:40]([NH:43][CH:44]([CH3:46])[CH3:45])([CH3:42])[CH3:41]>C(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]([S:8]([NH:11][C:12]2[S:13][C:14]([CH2:17][C:18]([N:43]([CH:44]([CH3:46])[CH3:45])[CH:40]([CH3:42])[CH3:41])=[O:20])=[CH:15][N:16]=2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 21980165HCID 21980165, compound

Product 1

HCID 10238158HCID 10238158, compoundYield 9.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1,3-thiazol-5-yl)acetic acid (Example 3) (0.09 g, 0.25 mmol) in CH2Cl2 (5.0 mL) and DMF (0.5 mL) were added EDCI (0.05 g, 0.27 mmol), DMAP (0.02 g, 0.12 mmol), triethylamine (0.1 mL, 0.75 mmol) and diisopropylamine (0.04 mL, 0.30 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then washed with 1 M HCl (2×15 mL) and the organic layer was collected. The organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification using preperative HPLC afforded the desired product (0.01 g) in 9% yield.

Workup

  1. washThe reaction mixture was then washed with 1 M HCl (2×15 mL)
  2. customthe organic layer was collected
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-38f1803929514a51a269f2c4ed9d2e97
Source dataset
uspto-grants-2006_08
Patent number
US07094792B2

Reaction notes

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