1-Hydroxybenzotriazole → HCID 11204460, compound

HRID 2376803Notes

Reaction equation

HRID 2376803 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([NH:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:28](O)=[O:29])[CH:24]=4)[N:19]=3)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:44][C@@H:45]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:46]([NH:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])=[O:47].C(N(C(C)C)CC)(C)C>C1COCC1.C(Cl)Cl.C(Cl)CCl>[CH2:49]([NH:48][C:46]([C@@H:45]([NH:44][C:28]([C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:17][C:15]([C:10]1[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:32])([F:31])[F:1])=[CH:8][CH:7]=3)=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:16])[CH:27]=[CH:26]2)=[O:29])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:47])[CH2:50][CH2:51][CH2:52][CH3:53]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 597109732-[[[4′-(Trifluoromethyl)[1,1′-biphenyl]-2-yl]carbonyl]amino]-6-quinolinecarboxylic acidHCID 69246396HCID 69246396, compound

Product 1

HCID 11204460HCID 11204460, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-6-carboxylic acid (F-1a2, 1.2 g, 2.53 mM), EDC (0.79 g, 6.34 mM), HOBT (0.86 g, 6.34 mM) and (S)-2-amino-N-pentyl-2-phenyl-acetamide hydrochloride (0.78 g, 3.05 mM) were combined and dissolved in THF (12.5 mL). The mixture was treated with diisopropylethylamine (2.20 mL, 13 mM) and stirred at room temperature for 16 h. The mixture was diluted with CH2Cl2 and washed with water. The CH2Cl2 fraction was dried (Na2SO4), filtered and concentrated. The product was purified by flash chromatography, eluting with 30% acetone in hexanes to give 1.36 g of (S)-2-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-6-carboxylic acid (pentylcarbamoyl-phenyl-methyl)-amide as an amorphous solid.

Workup

  1. washwashed with water
  2. dry with materialThe CH2Cl2 fraction was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by flash chromatography
  6. washeluting with 30% acetone in hexanes

Sources & evidence

ORD record
ord-9fccb9bb5e1c4657b710aa6c8aab2f8a
Source dataset
uspto-grants-2008_12
Patent number
US07468378B2

Reaction notes

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