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Diisopropylethylamine → HCID 44553916, compound

HRID 2359412
Notes
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Reaction equation

HRID 2359412 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH2:4][O:3]1.[F:17][C:18]([F:39])([F:38])[C:19]1[CH:20]=[C:21]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[C:28]([C:35](O)=[O:36])[CH:29]=[CH:30][CH:31]=3)[N:26]=2)[CH:22]=[CH:23][CH:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:13][C:35]([C:28]2[CH:29]=[CH:30][CH:31]=[C:32]3[C:27]=2[N:26]=[C:25]([C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:39])([F:17])[F:38])[CH:20]=2)[CH:34]=[CH:33]3)=[O:36])=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 575815714-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)anilineHCID 58154625HCID 58154625, compound

Product 1

HCID 44553916HCID 44553916, compound
Yield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of 4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)aniline (167 mg, 0.750 mmol), 2-(3-(trifluoromethyl)phenyl)quinoline-8-carboxylic acid (159 mg, 0.500 mmol), HATU (285 mg, 0.75 mmol) in NMP (5 mL) was added DIPEA (173 μL, 1.0 mmol). The reaction was stirred for 72 hours at room temperature, water (5 mL) was added and the resulting precipitates were collected by filtration and recrystallized from ethanol. The yellow solid was treated with a mixture of 1:3 6N HCl/Dioxane (8 mL) overnight. The mixture was concentrated to dryness, triturated with water, collected by filtration, washed with water and dried to obtain N-(4-(2,3-dihydroxypropoxy)phenyl)-2-(3-(trifluoromethyl)phenyl)quinoline-8-carboxamide (191 mg, 79% yield). MS (ESI) calcd for C26H21F3N2O4 (m/z): 482.15. found: 483 [M+1].

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. customrecrystallized from ethanol
  4. additionThe yellow solid was treated with a mixture of 1:3 6N HCl/Dioxane (8 mL) overnight
  5. concentrationThe mixture was concentrated to dryness
  6. customtriturated with water
  7. filtrationcollected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-ccd84f44314d48aeb98ad1fbbc66aab5
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08685970B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes