Cumylamine → ethyl 5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-1-carboxylate

HRID 448131Notes

Reaction equation

HRID 448131 reaction equation
[C:1]([NH2:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[CH2:34]([O:36][C:37]([N:39]1[C:43]2[S:44][C:45]([C:47](O)=[O:48])=[CH:46][C:42]=2[C:41]([NH:50][C:51](=[O:64])[C:52]2[CH:57]=[CH:56][C:55]([N:58]3[CH2:63][CH2:62][O:61][CH2:60][CH2:59]3)=[CH:54][CH:53]=2)=[N:40]1)=[O:38])[CH3:35].CCN(C(C)C)C(C)C>CN(C)C=O.O>[CH3:2][C:1]([NH:10][C:47]([C:45]1[S:44][C:43]2[N:39]([C:37]([O:36][CH2:34][CH3:35])=[O:38])[N:40]=[C:41]([NH:50][C:51](=[O:64])[C:52]3[CH:57]=[CH:56][C:55]([N:58]4[CH2:63][CH2:62][O:61][CH2:60][CH2:59]4)=[CH:54][CH:53]=3)[C:42]=2[CH:46]=1)=[O:48])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3]

Participants

7

Reactant 4

HCID 68509CumylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667857921-(ethoxycarbonyl)-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-5-carboxylic acid hydrochloride

Product 1

HCID 44520544ethyl 5-{[(1-methyl-1-phenylethyl)amino]carbonyl}-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-1-carboxylateYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of cumylamine (1.43 g, 10.6 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 3.40 g, 10.6 mmol), 1-(ethoxycarbonyl)-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-5-carboxylic acid hydrochloride (3.40 mg, 7.07 mmol) and N,N′-diisopropylethylamine (12.1 mL, 7.07 mmol) in 80 mL of dimethylformamide was stirred at room temperature for 20 hours. Afterward the reaction mixture was diluted with water and extracted with dichloromethane. Volatiles were removed by evaporation under reduced pressure and the residue was triturated with ethyl acetate, filtered, extensively washed with diethyl ether and dried under vacuum at 40° C., to give 3.7 g of the title compound, used in the next step without further purification.

Workup

  1. extractionextracted with dichloromethane
  2. customVolatiles were removed by evaporation under reduced pressure
  3. customthe residue was triturated with ethyl acetate
  4. filtrationfiltered
  5. washextensively washed with diethyl ether
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-29db0bf3015440778be39bfe1ff617d1
Source dataset
uspto-grants-2013_07
Patent number
US08481584B2

Reaction notes

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