Acetic Acid → HCID 53380259, compound

HRID 2176951Notes

Reaction equation

HRID 2176951 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([C:14]([NH:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[O:30][CH3:31])N=[CH:19][N:18]=2)=[O:15])[CH2:10]1.[CH3:32]C(O)=O.O>C(Cl)Cl>[C:1]([NH:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([C:14]([NH:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[O:30][CH3:31])[CH:32]=[CH:19][N:18]=2)=[O:15])[CH2:10]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 67382966HCID 67382966, compound

Product 1

HCID 53380259HCID 53380259, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.035 ml, 0.304 mmol) was added to a solution of (1S,3R)-3-Amino-N-(6-(4-fluoro-2-methoxyphenyl)pyrimidin-4-yl)cyclopentanecarboxamide (100 mg, 0.30 mmol) in DCM (5 ml) and catalytic amount of AcOH (0.1 ml) at 0° C. The reaction mixture was warmed to room temperature and stirred for 2.5 h. Water was added to the reaction mixture and extracted with DCM (3×25 ml). The combined organic layer was washed with water, brine and dried over anhydrous sodium sulfate and concentrated in vacuo to afford 90 mg (80.3%) of (1S,3R)-3-acetamido-N-(4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl)cyclopentanecarboxamide as an off white solid. 1H-NMR (400 MHz, DMSO-d6): δ=10.52 (s, 1H), 8.31 (s, 1H), 8.21 (s, 1H), 7.92 (t, 1H), 7.39-7.36 (m, 1H), 7.19-7.02 (m, 2H), 6.92 (q, 1H), 4.02 (t, 1H), 3.90 (s, 3H), 2.98 (t, 1H), 2.17-2.10 (m, 1H), 1.91-1.62 (m, 6H), 1.59-1.42 (m, 2H), HPLC (λ=214 nm, [A]): rt 10.4 min (100%), Chiral HPLC: 98.52%, mp: 125-129° C.

Workup

  1. extractionextracted with DCM (3×25 ml)
  2. washThe combined organic layer was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02b27ecb413f4aa39c43022301dc121b
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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