1,2-Dichloroethane → HCID 86723975, compound

HRID 1475365Notes

Reaction equation

HRID 1475365 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([CH2:17][C:18]([OH:20])=O)=[CH:11][C:12]([O:15][CH3:16])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:9]2=[CH:14][N:13]=[C:12]([O:15][CH3:16])[CH:11]=[C:10]2[CH2:17][C:18]1=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 86723976HCID 86723976, compound

Product 1

HCID 86723975HCID 86723975, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-tert-Butoxycarbonylamino-2-methoxy-pyridin-4-yl)-acetic acid (10 g, 35.4 mmol) was dissovled in DCM (142 mL) and EDC (7.5 g, 39 mmol), HOAt (5.4 g, 39 mmol) and DIPEA (15 mL, 85.7 mmol) were sequentially added, under N2. The reaction was stirred for 2 h at ambient temperature then quenched by addition of saturated aqueous NaHCO3 and extracted with DCM (×3). The combined organic extracts were washed with water and brine then dried over MgSO4 and concentrated in vacuo. The product was purified by column chromatography to yield the title compound (9.5 g) as a pale brown solid. 1H NMR (DMSO-c/6): 8.38 (1H, s), 6.83 (1H, s), 3.84 (3H, s), 3.77 (2H, s), 1.57 (9H, s). MS: [M+H]+=265.

Workup

  1. customthen quenched by addition of saturated aqueous NaHCO3
  2. extractionextracted with DCM (×3)
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialthen dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-21233b4501cc416da3197a362f9020e5
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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