Diisopropylethylamine → HCID 52916798, compound

HRID 2172972Notes

Reaction equation

HRID 2172972 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[N:14][CH:15]=[C:16]([C:17]([OH:19])=O)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[S:53]1[CH:57]=[N:56][N:55]=[C:54]1[C:58]1([NH2:61])[CH2:60][CH2:59]1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[S:53]1[CH:57]=[N:56][N:55]=[C:54]1[C:58]1([NH:61][C:17]([C:16]2[C:11]3[CH:10]=[N:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[C:12]=3[CH:13]=[N:14][CH:15]=2)=[O:19])[CH2:60][CH2:59]1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592781371-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acidHCID 67116043HCID 67116043, compound

Product 1

HCID 52916798HCID 52916798, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (90.0 mg, 0.350 mmol) in DMF (2 mL) is added N,N-diisopropylethylamine (243 μL, 1.40 mmol) and HBTU (159 mg, 0.420 mmol). After 20 minutes, a solution of 1-1,3,4-thiadiazol-2-yl-cyclopropylamine (51.0 mg, 0.361 mmol) in DMF (1 mL) is added and the mixture is stirred at room temperature overnight. The reaction mixture is poured into saturated aqueous sodium bicarbonate (50 mL), ethyl acetate (30 mL) is added and phases are separated. The aqueous layer is treated with brine and extracted with ethyl acetate (3×20 mL). The combined organic layers are concentrated in vacuo. The crude material is purified by silica gel chromatography eluting with a gradient of 0-10% methanol in methylene chloride to afford the title compound as a solid.

Workup

  1. additionis added
  2. customphases are separated
  3. additionThe aqueous layer is treated with brine
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. concentrationThe combined organic layers are concentrated in vacuo
  6. customThe crude material is purified by silica gel chromatography
  7. washeluting with a gradient of 0-10% methanol in methylene chloride

Sources & evidence

ORD record
ord-d116caf7b48a4878a1a23391139bf2f3
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

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