1,2-Dichloroethane → (2-{[2-(3-Sulfamoyl-phenylamino)-thieno[2,3-h]quinazoline-8-carbonyl]amino}-ethyl)-carbamic acid tert-butyl ester

HRID 643743Notes

Reaction equation

HRID 643743 reaction equation
[S:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:21]=[CH:20][C:19]3[C:14](=[C:15]4[CH:24]=[C:23]([C:25]([OH:27])=O)[S:22][C:16]4=[CH:17][CH:18]=3)[N:13]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])(=[O:3])[NH2:2].ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:47]([NH:54][CH2:55][CH2:56][NH2:57])([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48].C(Cl)CCl>CN(C=O)C>[C:50]([O:49][C:47](=[O:48])[NH:54][CH2:55][CH2:56][NH:57][C:25]([C:23]1[S:22][C:16]2=[CH:17][CH:18]=[C:19]3[C:14]([N:13]=[C:12]([NH:11][C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([S:1](=[O:3])(=[O:4])[NH2:2])[CH:6]=4)[N:21]=[CH:20]3)=[C:15]2[CH:24]=1)=[O:27])([CH3:53])([CH3:51])[CH3:52]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 187201N-BOC-ethylenediamineHCID 59262912HCID 59262912, compound

Product 1

HCID 59262928(2-{[2-(3-Sulfamoyl-phenylamino)-thieno[2,3-h]quinazoline-8-carbonyl]amino}-ethyl)-carbamic acid tert-butyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3-Sulfamoyl-phenylamino)-thieno[2,3-h]quinazoline-8-carboxylic acid (150 mg, 0.37 mmol), 1-hydroxy-7-azabenzotriazole (56 mg, 0.41 mmol), N,N-diisopropylethylamine (73 mg, 0.56 mmol) and BOC-ethylenediamine (66 mg, 0.41 mmol) were dissolved in dry DMF (2 mL) and cooled in an ice-bath. EDC (79 mg, 0.41 mmol) was added in one portion and the resultant suspension was stirred overnight allowing the ice-bath to melt. The reaction was concentrated under reduced pressure, redissolved in isopropanol (˜10 mL) and water was added (˜5 mL). The precipitate formed was isolated by filtration and washed with water (1×5 mL), dilute NaHSO4 (1×5 mL), water (1×5mL), saturated Na2CO3 (1×5 mL), water (1×5mL), isopropanol (1×5 mL), diethyl ether (2×5 mL) and pentane (2×5 mL) giving an ochre powder (102 mg, 51% yield). MS (ES+) 543. δH (d6 DMSO) 1.2-1.5 (9H, s), 3.3-3.5 (4H, br m), 6.6 (0.1 H, br s), 7.0 (0.9H, br s), 7.1-7.4 (2H, br s), 7.4-7.6 (2H, m), 7.8-8.0 (2H, m), 8.2 (1H, m), 8.6-9.0 (3H, br m), 9.4 (1H, s), 10.3-10.6 (1H, br s).

Workup

  1. temperaturecooled in an ice-bath
  2. concentrationThe reaction was concentrated under reduced pressure
  3. dissolutionredissolved in isopropanol (˜10 mL)
  4. additionwater was added (˜5 mL)
  5. customThe precipitate formed
  6. customwas isolated by filtration
  7. washwashed with water (1×5 mL), dilute NaHSO4 (1×5 mL), water (1×5mL), saturated Na2CO3 (1×5 mL), water (1×5mL), isopropanol (1×5 mL), diethyl ether (2×5 mL) and pentane (2×5 mL)

Sources & evidence

ORD record
ord-09cc1c3f8aae404291b4e6b52f3fe600
Source dataset
uspto-grants-2010_04
Patent number
US07700609B2

Reaction notes

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