Diisopropylethylamine → {5-Bromo-2-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenylcarbamoyl]thiophen-3-yl}carbamic acid tert-butyl ester

HRID 532431Notes

Reaction equation

HRID 532431 reaction equation
[B-](F)(F)(F)F.C[CH2:7][O:8][C:9]([C:11]([C:21]#[N:22])=NOC(N(C)C)=[N+](C)C)=O.C(N(CC)C(C)C)(C)C.[Br:32][C:33]1[S:37][C:36]([C:38]([OH:40])=O)=[C:35]([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH:34]=1.CONC1C=C[C:55]([O:58][CH2:59][CH2:60][N:61]2[CH2:65][CH2:64][CH2:63][CH2:62]2)=[CH:54][CH:53]=1>CN(C=O)C.C(OCC)(=O)C>[C:45]([O:44][C:42](=[O:43])[NH:41][C:35]1[CH:34]=[C:33]([Br:32])[S:37][C:36]=1[C:38](=[O:40])[NH:22][C:21]1[CH:53]=[CH:54][C:55]([O:58][CH2:59][CH2:60][N:61]2[CH2:62][CH2:63][CH2:64][CH2:65]2)=[C:9]([O:8][CH3:7])[CH:11]=1)([CH3:48])([CH3:47])[CH3:46]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 219758545-Bromo-3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylic acidHCID 86628783Methoxy-4-(2-pyrrolidin-1-ylethoxy)phenylamine

Product 1

HCID 68940005{5-Bromo-2-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenylcarbamoyl]thiophen-3-yl}carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

TOTU (327.3 mg) and N,N-diisopropylethylamine (122.8 mg) were added to a mixture of 5-bromo-3-tert-butoxycarbonylaminothiophene-2-carboxylic acid (306.1 mg), methoxy-4-(2-pyrrolidin-1-ylethoxy)phenylamine (224.5 mg) in DMF (3.8 mL). The reaction mixture was stirred at room temperature overnight. Ethyl acetate was then added, and the organic phase was washed with 10% strength citric acid and saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and concentrated. The product with the molecular weight of 539.11 (C23H30BrN3O5S) was obtained in this way; MS (ESI): 540, 542 (M+H+).

Workup

  1. washthe organic phase was washed with 10% strength citric acid and saturated sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe product with the molecular weight of 539.11 (C23H30BrN3O5S) was obtained in this way

Sources & evidence

ORD record
ord-89395a65deee4b49879a47f6c7533cd6
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Reaction notes

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