Triethylamine → HCID 58864195, compound

HRID 1353452Notes

Reaction equation

HRID 1353452 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][C@@H:21]([CH3:25])[C:22](O)=[O:23])=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:26])=[CH:7][CH:8]=2)[N:3]=1.CC[N:29]([CH2:32][CH3:33])CC.CN(C(ON1N=N[C:44]2[CH:45]=[CH:46]C=N[C:43]1=2)=[N+](C)C)C.[F:51][P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl.CO>[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]([NH:20][C@@H:21]([CH3:25])[C:22]([NH:29][C:32]3[CH:33]=[CH:43][C:44]([F:51])=[CH:45][CH:46]=3)=[O:23])=[O:19])[CH2:16][CH2:17]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:26])=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58864166HCID 58864166, compound

Product 1

HCID 58864195HCID 58864195, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of (2S)-2-[[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]-propanoic acid (˜30 mg), 4-fluoroanaline (0.03 mL, 0.32 mmol), Et3N (0.14 mL, 0.35 mmol) in DMF (2 mL) was added HATU (133 mg, 0.35 mmol) at rt. After stirring at rt overnight, the reaction mixture was poured into ice-water. The crude solid was obtained by filtration and re-dissolved in CH2Cl2-MeOH, dried over Na2SO4. Concentration in vacuo followed by preparative TLC(CH2Cl2-MeOH-Et3N, 9:1:1%) afforded the title product as a light yellow powder. LC-MS: 471 (M++1). 1H NMR (DMSO-d6): δ 1.30 (d, 3H), 3.00 (br.s, 4H), 3.58 (m, 4H), 4.28 (m, 1H), 6.26 (s, 1H), 6.60 (br.s, 2H), 6.30 (d, 1H), 7.16 (m, 3H), 7.40 (d, 1H), 7.63 (dd, 2H), 7.75 (d, 1H).

Workup

  1. customThe crude solid was obtained by filtration
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-fdb36b2f79524763aacb30d5c2ff19a4
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

Loading…