Diisopropylethylamine → HCID 86720864, compound

HRID 1528141Notes

Reaction equation

HRID 1528141 reaction equation
[NH2:1][C:2]1[C:3]([O:8][CH:9]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)=[N:4][CH:5]=[N:6][CH:7]=1.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[C:29]1[S:30][CH:31]=[C:32]([C:34](O)=[O:35])[N:33]=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>CN(C=O)C.C(OCC)(=O)C>[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[C:29]1[S:30][CH:31]=[C:32]([C:34]([NH:1][C:2]2[C:3]([O:8][CH:9]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]3)=[N:4][CH:5]=[N:6][CH:7]=2)=[O:35])[N:33]=1

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 242784542-(2,6-Difluorophenyl)-1,3-thiazole-4-carboxylic acidHCID 86720863Tert-butyl 3-((5-aminopyrimidin-4-yl)oxy)pyrrolidine-1-carboxylate

Product 1

HCID 86720864HCID 86720864, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Compound (1D3) (47 mg, 0.169 mmol), 2-(2,6-difluorophenyl)thiazole-4-carboxylic acid (1E) (40 mg, 0.169 mmol, HATU (77 mg, 0.203 mmol) and DIEA (93 μL, 0.507 mmol) are mixed in DMF (5 mL) and stirred at 50° C. for 1 hour. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (50 mL), washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified with flash column (eluent: 10-30% ethyl acetate/petroleum ether) to obtain the product 1A (30 mg, 0.0596 mmol)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with flash column (eluent: 10-30% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-6b957e8546524d62a45f26487f4c6596
Source dataset
uspto-grants-2015_07
Patent number
US09090594B2

Reaction notes

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