Diisopropylethylamine → HCID 70980685, compound

HRID 1754117Notes

Reaction equation

HRID 1754117 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)[CH:2]=1.Cl.[CH3:13][N:14](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.N1C=CC=C(/C=C/C(N[C:55]2[CH:60]=[CH:59][C:58]([S:61](=[O:75])(=[O:74])[NH:62][C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=3[O:69]C(F)(F)F)=[CH:57][CH:56]=2)=O)C=1>O1CCCC1>[CH:67]12[O:69][CH:64]([CH2:65][CH2:66]1)[CH2:63][N:62]([S:61]([C:58]1[CH:57]=[CH:56][C:55]([CH2:13][NH:14][C:9](=[O:11])/[CH:8]=[CH:7]/[C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:60][CH:59]=1)(=[O:74])=[O:75])[CH2:68]2

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 71007329HCID 71007329, compound

Product 1

HCID 70980685HCID 70980685, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 25 mL round-bottomed flask was added (E)-3-(pyridin-3-yl)acrylic acid (38.0 mg, 0.255 mmol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (48.9 mg, 0.255 mmol) and 1-Hydroxybenzotriazole hydrate (39.0 mg, 0.255 mmol) in Tetrahydrofuran (Volume: 4 ml) to give a light yellow suspension. Diisopropylethylamine (0.089 ml, 0.510 mmol) and (4-(8-oxa-3-azabicyclo[3.2.1]octan-3-ylsulfonyl)phenyl)methanamine (48 mg, 0.170 mmol; prepared according to example 5) were added sequentially and the suspension was allowed to stir at room temperature overnight before being filtered through Celite®. The cake was washed with THF then the combined filtrate was concentrated in vacuo and the resulting residue was purified by Preparative-HPLC to afford the product (68.0 mg).

Workup

  1. customto give a light yellow suspension
  2. filtrationbefore being filtered through Celite®
  3. washThe cake was washed with THF
  4. concentrationthe combined filtrate was concentrated in vacuo
  5. customthe resulting residue was purified by Preparative-HPLC

Sources & evidence

ORD record
ord-ae474f3f0dc74155993bb5e2d97be49f
Source dataset
uspto-grants-2015_10
Patent number
US09169209B2

Reaction notes

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