Cumylamine → HCID 57737267, compound

HRID 549433Notes

Reaction equation

HRID 549433 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:10]2[S:11][C:12]([C:14](O)=[O:15])=[CH:13][C:9]=2[C:8]([NH:17][C:18](=[O:33])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[NH:29][CH:30]=[CH:31][CH:32]=2)=[O:27])=[N:7]1)=[O:5])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[C:65]([NH2:74])([C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1)([CH3:67])[CH3:66]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4]([N:6]1[C:10]2[S:11][C:12]([C:14](=[O:15])[NH:74][C:65]([CH3:67])([C:68]3[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=3)[CH3:66])=[CH:13][C:9]=2[C:8]([NH:17][C:18](=[O:33])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[NH:29][CH:30]=[CH:31][CH:32]=2)=[O:27])=[N:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 68509CumylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57737264HCID 57737264, compound

Product 1

HCID 57737267HCID 57737267, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-{2-[(1H-Pyrrole-2-carbonyl)-amino]-benzoylamino}-thieno[2,3-c]pyrazole-1,5-dicarboxylic acid 1-ethyl ester (198.5 mg, 0.4246 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 204 mg, 0.6369 mmol), DIEA (0.29 mL, 1.6984 mmol) and cumylamine (115 mg, 0.8492 mmol) in DMF (10 mL) was stirred at room temperature. After 2 hours the mixture was diluted with AcOEt (40 mL) and washed with saturated NaHCO3, water and brine. The organic layer was dried over Na2SO4 and evaporated to give 495 mg of crude that was used in the next step without further purification, LC-MS: Rt 7.36; [M+H]+ 585.

Workup

  1. washwashed with saturated NaHCO3, water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated
  4. customto give 495 mg of crude that
  5. customwas used in the next step without further purification, LC-MS

Sources & evidence

ORD record
ord-0cca8dc2289842eea1b6bd14e2ea49e5
Source dataset
uspto-grants-2011_05
Patent number
US07943654B2

Reaction notes

Loading…