1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-2-oxo-2-(thiophen-2-sulfonylamino)-acetamide

HRID 1817996

Reaction equation

HRID 1817996 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[C:17]2[C:18]([NH:22][C:23](=[O:27])[C:24]([OH:26])=O)=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:28].[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[S:34]([NH2:37])(=[O:36])=[O:35].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(Cl)(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[C:17]2[C:18]([NH:22][C:23](=[O:27])[C:24](=[O:26])[NH:37][S:34]([C:30]3[S:29][CH:33]=[CH:32][CH:31]=3)(=[O:36])=[O:35])=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:28]

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 728812-ThiophenesulfonamideHCID 66917711N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-oxalamic acid

Product 1

HCID 66917653N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-2-oxo-2-(thiophen-2-sulfonylamino)-acetamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-oxalamic acid, I-62 (52 mg, 0.14 mmol), thiophene sulfonamide (28 mg, 0.17 mmol), EDCI (33 mg, 0.17 mmol), DMAP (22 mg, 0.17 mmol) in methylene chloride was stirred at room temperature for 24 h. Reaction was diluted with chloroform (10 mL) and washed with 6.0 M HCl (3.0 mL×4), water (3.0 mL). Chloroform layer was concentrated and the residue was purified over silica gel with chloroform:methanol (90:10) as eluant to afford N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-2-oxo-2-(thiophen-2-sulfonylamino)-acetamide, P019 (7.0 mg). 1H NMR (500 MHz, DMSO-d6) 4.59 (s, 2H), 5.35 (s, 2H), 6.84 (dd, J=8.0, 1.5 Hz, 1H), 6.90 (dd, J=8.0, 8.0 Hz, 1H), 7.02 (m, 2H), 7.06 (dd, J=5.0, 3.5 Hz, 1H), 7.44 (m, 1H), 7.56 (s, 1H), 7.61 (dd, J=3.5, 1.5 Hz, 1H), 7.71-7.65 (m, 3H), 7.78 (m, 1H), 10.05 (s, 1H). MS (ESI−) Calcd. (M+) 521.6; Found: 520.7 (M−1).

Workup

  1. customReaction
  2. washwashed with 6.0 M HCl (3.0 mL×4), water (3.0 mL)
  3. concentrationChloroform layer was concentrated
  4. customthe residue was purified over silica gel with chloroform:methanol (90:10) as eluant

Sources & evidence

ORD record
ord-97bdea40ab6848d593ff40e55ceeff72
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Linked notes

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