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Triethylamine → HCID 178522149, compound

HRID 1094485
Notes
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Reaction equation

HRID 1094485 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19](O)=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:3]=1.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][C:24]=1[C:30]([F:33])([F:32])[F:31].CCN(CC)CC.CCCP(=O)=O>CN(C1C=CN=CC=1)C.CN(C=O)C.[Cl-].[Na+].O.CCOC(C)=O.O>[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:19]([C:15]2[C:16]3[C:11](=[CH:10][C:9]([CH2:8][C:4]4[CH:3]=[C:2]([OH:1])[N:7]=[CH:6][N:5]=4)=[CH:18][CH:17]=3)[CH:12]=[CH:13][CH:14]=2)=[O:20])=[CH:25][C:24]=1[C:30]([F:31])([F:32])[F:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 16167369Propylphosphoric anhydrideHCID 178524206HCID 178524206, compound

Product 1

HCID 178522149HCID 178522149, compound

Reagents, catalysts & solvents 5

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent
HCID 57417360Sodium chloride; waterSolvent

Procedure

345 mg (1.23 mMol) 6-(6-hydroxy-pyrimidin-4-ylmethyl)-naphthalene-1-carboxylic acid (Step 3.8), 193 μl (1.5 mMol) 4-fluoro-3-trifluoromethyl-aniline, 1.7 ml (12.3 mMol) Et3N and 63 mg (0.52 mMol) DMAP are dissolved in 10 ml of dry DMF. Then a solution of 1.45 ml (50% in DMF; 2.48 mMol) propylphosphonic anhydride is added. After 20 min, the reaction mixture is poured into water, brine and EtOAc. The separated aq. phase is extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; CH2Cl2→CH2Cl2/MeOH 1:19) gives the title compound: MS: [M+1]+=442; TLC (CH2Cl2/MeOH 1:9): Rf=0.37; 1H-NMR (DMSO-d6): δ ppm 12.43 (s, 1H), 10.92 (s, HN), 8.36 (m, 1H), 8.17 (d, 1H), 8.11 (m, 3H), 7.92 (s, 1H), 7.78 (d, 1H), 7.7-7.5 (m, 3H), 6.25 (s, 1H), 3.99 (s, H2C).

Workup

  1. extractionThe separated aq. phase is extracted twice with EtOAc
  2. washThe organic layers are washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d5ac67afc2c349a99ebb78871b723a9c
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08133886B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes