Triethylamine → 7-Chloro-4-[4-[(4-fluorophenyl)acetyl]-1-piperazinyl]-2-quinolinamine

HRID 1353441Notes

Reaction equation

HRID 1353441 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([NH2:13])[CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=O)=[CH:17][CH:16]=1.CN(C(ON1N=[N:40][C:35]2C=[CH:37][CH:38]=[N:39][C:34]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:39]3[CH2:34][CH2:35][N:40]([C:22](=[O:24])[CH2:21][C:18]4[CH:17]=[CH:16][C:15]([F:14])=[CH:20][CH:19]=4)[CH2:37][CH2:38]3)=[CH:3][C:4]([NH2:13])=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 140674082-Amino-4,7-dichloroquinoline

Product 1

HCID 211017697-Chloro-4-[4-[(4-fluorophenyl)acetyl]-1-piperazinyl]-2-quinolinamine

Procedure

To a stirred solution of 4,7-dichloro-2-quinolinamine (50 mg, 0.19 mmol) in DSMO (10 mL) was added 4-fluorobenzeneacetic acid (32 mg, 0.2 mmol) followed by HATU (94 mg, 0.25 mmol) and triethylamine (0.053 ml, 0.38 mmol) at rt. After stirring overnight, the reaction mixture was poured into ice-water (10 mL), extracted with EtOAc, washed with brine, and dried over Na2SO4. Concentration in vacuo followed by preemptive TLC afforded the product. LC-MS: 398 (M++1)). 1H NMR (DMSO-d6): 62.9–3.05 (m, 4H), 3.68–3.85 (m, 6H), 6.22 (s, 1H), 6.45 (s, 2H), 7.05–7.2 (m, 3H), 7.22–7.33 (m, 2H), 7.35–7.4 (m, 1H), 7.7–7.8 (d, 1H).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration in vacuo
  5. customafforded the product

Sources & evidence

ORD record
ord-5702965d4b144f19be8c2fd9c26a5572
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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