Diisopropylethylamine → HCID 178490960, compound

HRID 230863Notes

Reaction equation

HRID 230863 reaction equation
F[C:2](F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([S:27]([CH:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)(=[O:29])=[O:28])[CH:25]=3)[N:20]=[CH:19][C:18]=2[C:36]([NH2:38])=[O:37])[CH:13]=[CH:14][CH:15]=1.[NH:39]1[CH:43]=[C:42]([C:44]([OH:46])=O)[N:41]=[CH:40]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[NH:39]1[CH:43]=[C:42]([C:44]([N:33]2[CH2:32][CH2:31][CH:30]([S:27]([C:24]3[CH:25]=[C:26]4[C:21](=[C:22]([CH3:2])[CH:23]=3)[N:20]=[CH:19][C:18]([C:36]([NH2:38])=[O:37])=[C:17]4[NH:16][C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH3:8])[CH:11]=3)(=[O:28])=[O:29])[CH2:35][CH2:34]2)=[O:46])[N:41]=[CH:40]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 674237274-{[3-(Methyloxy)phenyl]amino}6-(4-piperidinylsulfonyl)-3-quinolinecarboxamide trifluoroacetateHCID 178524800HCID 178524800, compound

Product 1

HCID 178490960HCID 178490960, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing Intermediate 54 (0.041 g) in N,N-dimethylformamide (3 ml) were added imidazole-4-carboxylic acid (0.012 g, Aldrich), (1H-1,2,3-benzotriazol-1-yloxy)(tri-1-pyrrolidinyl)phosphonium hexafluorophosphate (PyBop) (0.053 g) and N,N-diisopropylethylamine (0.03 ml). The solution was stirred under nitrogen at room temperature for 18 h and was then concentrated in vacuo. The residual gum was purified using an aminopropyl SPE cartridge eluting with methanol followed by chromatography on silica gel (SPE cartridge), eluting with a gradient of 0% to 8% methanol in chloroform, to give the title compound as a yellow solid (0.031 g).

Workup

  1. concentrationwas then concentrated in vacuo
  2. customThe residual gum was purified
  3. washeluting with methanol
  4. washeluting with a gradient of 0% to 8% methanol in chloroform

Sources & evidence

ORD record
ord-5c65edbc41a04faab316338d1917f5ec
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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