Diisopropylethylamine → HCID 68946114, compound

HRID 2103777Notes

Reaction equation

HRID 2103777 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([C:5]1[S:6][C:7]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:8]=2[C:9]=1[CH2:10][C:11]([OH:13])=[O:12])=O.C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:2]([C:3]1[O:12][C:11](=[O:13])[CH:10]=[C:9]2[C:8]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:7]=3[S:6][C:5]=12)([CH3:21])([CH3:20])[CH3:1]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68949271HCID 68949271, compound

Product 1

HCID 68946114HCID 68946114, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A round bottom flask was charged with 0.460 g [2-(2,2-dimethylpropanoyl)-5-methoxy-1-benzothien-3-yl]acetic acid from the Step C above, 0.345 g HOBt hydrate, and 0.504 g EDC HCl salt. This mixture was dissolved in 15 mL anhydrous DMF and 0.582 g DIEA was added. The mixture turned bright yellow. After standing at room temperature overnight, the mixture was poured into water and extracted with ether several times. The combined ether extract was washed with water (4×), 5% NaHCO3, and saturated brine, dried over anhydrous Na2SO4, and evaporated to give the title compound as a bright yellow solid. 1H NMR (CDCl3, 500 MHz) 7.49 (d, 8.7 Hz, 1H), 7.35 (d, 2.5 Hz, 1H), 7.20 (dd, 2.5 & 8.9 Hz, 1H), 6.65 (s, 1H), 3.92 (s, 3H), 1.51 (s, 9H). LC-MS: 3.77 min. (m/Z=289.3).

Workup

  1. extractionextracted with ether several times
  2. extractionThe combined ether extract
  3. washwas washed with water (4×), 5% NaHCO3, and saturated brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-68474a93f8d842ca959e9ea9214cff25
Source dataset
uspto-grants-2009_08
Patent number
US07576122B2

Reaction notes

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