Triethylamine → tert-Butyl 2-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethylcarbamate

HRID 1261355Notes

Reaction equation

HRID 1261355 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14](Cl)=[O:15])[S:13][C:6]=12.Cl.[C:25]([N:32](C)[CH2:33][CH2:34][NH2:35])([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([NH:35][CH2:34][CH2:33][NH:32][C:25](=[O:26])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:15])[S:13][C:6]=12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 45072251tert-Butyl (2-aminoethyl)methylcarbamate--hydrogen chloride (1/1)HCID 594245267-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carbonyl chloride

Product 1

HCID 59424685tert-Butyl 2-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxamido)ethylcarbamateYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 40 (shown in the scheme 7, 100 mg, 0.26 mmol), N-Boc-N-methylethylenediamine hydrochloride (50 mg, 0.26 mmol) and Et3N (36 μL, 0.52 mmol) in DCM (2 mL) was stirred for 4 h at room temperature and diluted with EtOAc (10 mL). The combined mixture was washed with brine and phases were separated. The aqueous phase was extracted with EtOAc, and the extract was combined with the organic phase, dried over anhydrous Na2SO4 and concentrated to afford title compound 292 (119 mg, 96%, crude) as yellowish solid. MS (m/z): 477.1 (M+H) (found).

Workup

  1. washThe combined mixture was washed with brine and phases
  2. customwere separated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1d924b1ea8ab4fbbbfcb75532308d731
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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