Acetic Acid → HCID 59753603, compound

HRID 751724Notes

Reaction equation

HRID 751724 reaction equation
[C:1](O)(=[O:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:26][CH:27]1[CH2:32][CH2:31][N:30]([C:33](=[O:56])[C@@H:34]([NH:43][C:44]([C:46]2[NH:55][C:49]3=[CH:50][N:51]=[C:52]([Cl:54])[CH:53]=[C:48]3[CH:47]=2)=[O:45])[CH2:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH2:29][CH2:28]1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]([NH:26][CH:27]1[CH2:28][CH2:29][N:30]([C:33](=[O:56])[C@@H:34]([NH:43][C:44]([C:46]2[NH:55][C:49]3=[CH:50][N:51]=[C:52]([Cl:54])[CH:53]=[C:48]3[CH:47]=2)=[O:45])[CH2:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH2:31][CH2:32]1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59753591HCID 59753591, compound

Product 1

HCID 59753603HCID 59753603, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of acetic acid (7.5 μL, 0.13 mmol) in DMF (5 mL) was added EDCI (33 mg, 0.17 mmol), HOBt (19.5 mg, 0.14 mmol), 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(4-aminopiperidin-1-yl)-1-(S)-(4-fluorobenzyl)-2-oxoethyl]amide (EXAMPLE 180, 70 mg, 0.16 mmol) and DIPEA (57 μL, 0.33 mmol), and the reaction stirred at rt for 16 h. Solvent was removed in vacuo then crude material partitioned between ethyl acetate (15 mL) and water (15 mL). The organic layer was washed with NaHCO3 (2×20 mL) and brine (2×30 mL), dried (MgSO4) and the solvent removed in vacuo. Purification by chromatography using dichloromethane/methanol (95:5) as the eluent gave the title compound as an off-white powder. m/z (ES+)=486.27 [M+H]+; RT=3.16 min.

Workup

  1. customSolvent was removed in vacuo
  2. customcrude material partitioned between ethyl acetate (15 mL) and water (15 mL)
  3. washThe organic layer was washed with NaHCO3 (2×20 mL) and brine (2×30 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-e75487a58b444639a6d73ded625800b7
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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