Triethylamine → HCID 90412449, compound

HRID 1522038Notes

Reaction equation

HRID 1522038 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:7][C:6]([C:8]2[NH:25][C:11]3=[N:12][CH:13]=[CH:14][C:15]([C:16]4[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=4[O:23][CH3:24])=[C:10]3[CH:9]=2)=[CH:5][CH2:4][NH:3]1.Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(N(CC)CC)C>CN(C)C=O>[F:22][C:20]1[CH:19]=[CH:18][C:17]([O:23][CH3:24])=[C:16]([C:15]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:25][C:8]([C:6]4[CH2:7][C:2]([CH3:26])([CH3:1])[N:3]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:4][CH:5]=4)=[CH:9][C:10]=23)[CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 90412266HCID 90412266, compound

Product 1

HCID 90412449HCID 90412449, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 272B (0.388 g, 0.915 mmol), tert-butyl bromoacetate (0.264 g, 1.35 mmol) and triethylamine (0.7 mL, 5.02 mmol) in N,N-dimethylformamide (2 mL) was heated at 70° C. for 8 hours and was concentrated. The residue was partitioned between ethyl acetate and water and the organic layer was dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel eluting with 50% ethyl acetate in hexanes gave the title compound. MS (ESI) m/e 466.4 (M+1)1.

Workup

  1. concentrationwas concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel eluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a9abc26d4ac14fc39892f56b1396dc6d
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

Loading…