Acetic Anhydride → HCID 86695456, compound

HRID 1520508Notes

Reaction equation

HRID 1520508 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([OH:25])[C@H:16]([NH:19][C:20](=[O:24])[CH:21]([Cl:23])[Cl:22])[CH2:17][F:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>C(Cl)Cl.O>[C:33]([NH:1][CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([C@@H:15]([OH:25])[C@H:16]([NH:19][C:20](=[O:24])[CH:21]([Cl:23])[Cl:22])[CH2:17][F:18])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86695381HCID 86695381, compound

Product 1

HCID 86695456HCID 86695456, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of crude N-{(1S,2R)-2-[4-(6-Aminomethyl-pyridin-3-yl)-phenyl]-1-fluoromethyl-2-hydroxy-ethyl}-2,2-dichloro-acetamide (30 mg, 0.077 mmol) in CH2Cl2 (2 mL) is added triethyl amine (8 mg, 0.078 mmol) and acetic anhydride (20 mg, 0.198) and the reaction mixture was stirred at room temperature for 6 h. Diluted with water and extracted with CH2Cl2 dried over sodium sulphate and solvent is evaporated in vacuo to give crude, which is purified by silica gel prep TLC using the mobile phase 10% methanol in CH2Cl2 to afford title compound (5 mg): 1H-NMR (400 MHz, DMSO-d6) 6: (s, 3H), 4.30-4.34 (m, 1H), 4.45 (d, J=5.96 Hz, 2H), 4.48-4.51 (m, 1H), 4.55-4.58 (m, 1H), 5.00 (d, 1H), 5.95 (d, 1H), 6.12 (s, 1H), 6.99 (bs, 1H), 7.34-7.36 (m, 1H), 7.47-7.50 (m, 2H), 7.62-7.67 (m, 2H), 7.96 (dd, J1=8.2 Hz, J2=2.4 Hz, 1H), 8.76 (d, J=2.2 Hz, 1H). LC-Ms (m/z): [M+H]=428.10.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over sodium sulphate and solvent
  3. customis evaporated in vacuo
  4. customto give crude, which
  5. customis purified by silica gel prep TLC

Sources & evidence

ORD record
ord-8dff8f57951243d896fdbcd8eeb7179f
Source dataset
uspto-grants-2015_07
Patent number
US09073894B2

Reaction notes

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