Cyclopropylamine → HCID 25119990, compound

HRID 2261260Notes

Reaction equation

HRID 2261260 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:13]2[N:14]([CH3:30])[C:15](=[O:29])[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=3[CH2:27][OH:28])[C:21]([OH:23])=O)=[CH:17][C:12]=2[CH:11]=[N:10]1.[CH:31]1([NH2:34])[CH2:33][CH2:32]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[CH:31]1([NH:34][C:21](=[O:23])[C:20]2[CH:24]=[CH:25][C:26]([CH2:27][OH:28])=[C:18]([C:16]3[C:15](=[O:29])[N:14]([CH3:30])[C:13]4[N:9]([C:3]5[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=5[F:1])[N:10]=[CH:11][C:12]=4[CH:17]=3)[CH:19]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68778513HCID 68778513, compound

Product 1

HCID 25119990HCID 25119990, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(1-(2,6-difluorophenyl)-7-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-5-yl)-4-(hydroxymethyl)benzoic acid (310 mg, 754 μmol) was treated with cyclopropanamine (0.21 mL, 3014 μmol) and HATU (430 mg, 1130 μmol) in THF (5.00 mL) under nitrogen and allowed to stir at RT. After 2 h the reaction was quenched by the addition of 1N NaOH (10 mL). The reaction mixture was extracted with EtOAc (2×25 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified on the ISCO 12 g column (70-100% EtOAc in hexanes) affording the title compound as an amorphous white solid. MS (ESI, pos.ion) m/z: 451.1 (M+1).

Workup

  1. customAfter 2 h the reaction was quenched by the addition of 1N NaOH (10 mL)
  2. extractionThe reaction mixture was extracted with EtOAc (2×25 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified on the ISCO 12 g column (70-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bbd9db7650ee40148c098aafcb3c8c98
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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