Triethylamine → HCID 67296697, compound

HRID 1969424Notes

Reaction equation

HRID 1969424 reaction equation
[C:1]1([NH:7][C:8]([C:10]2([C:13]([OH:15])=O)[CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N:17](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:40]([O:47][C:48]1[CH:57]=[C:56]2[C:51]([C:52]([O:58][C:59]3[CH:64]=[CH:63][C:62](N)=[CH:61][C:60]=3[F:66])=[CH:53][CH:54]=[N:55]2)=[CH:50][CH:49]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.CCN(CC)CC>C(Cl)Cl>[CH2:40]([O:47][C:48]1[CH:57]=[C:56]2[C:51]([C:52]([O:58][C:59]3[CH:64]=[CH:63][C:62]([N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:8]([C:10]4([C:13]([NH2:17])=[O:15])[CH2:11][CH2:12]4)=[O:9])=[CH:61][C:60]=3[F:66])=[CH:53][CH:54]=[N:55]2)=[CH:50][CH:49]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 190968711-(Phenylcarbamoyl)cyclopropanecarboxylic acidHCID 66669917HCID 66669917, compound

Product 1

HCID 67296697HCID 67296697, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(phenylcarbamoyl)cyclopropanecarboxylic acid (1.14 g, 5.6 mmol) in dry CH2Cl2 (8 mL) was added HATU (2.11 g, 5.6 mmol) at 0° C. After stirring for 10 minutes, a solution of the 4-(7-(benzyloxy)quinolin-4-yloxy)-3-fluorobenzenamine (1.0 g, 2.8 mmol) and Et3N (0.7 g, 6.9 mmol) in dry CH2Cl2 (5 mL) was added. The reaction mixture was stirred at 40° C. for 24 hrs, quenched with water (10 mL), and extracted with CH2Cl2 (30 mL×3). The combined organic phases were dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuo. The residue was chromatographed with a silica gel column (1:1 (v/v) EtOAc/n-hexane) to afford the title compound as a white solid (1.3 g, 85%).

Workup

  1. stirringThe reaction mixture was stirred at 40° C. for 24 hrs
  2. customquenched with water (10 mL)
  3. extractionextracted with CH2Cl2 (30 mL×3)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was chromatographed with a silica gel column (1:1 (v/v) EtOAc/n-hexane)

Sources & evidence

ORD record
ord-e985a461d25347adb10014c25e5f722d
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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