Cyclopropylamine → HCID 67975549, compound

HRID 537848Notes

Reaction equation

HRID 537848 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH2:24][CH2:25][CH2:26][CH2:27][F:28])[C:7]([CH2:9][N:10]3[C:14]4[CH:15]=[N:16][CH:17]=[CH:18][C:13]=4[N:12]([CH2:19][C:20](O)=[O:21])[C:11]3=[O:23])=[N:8][C:4]=2[CH:3]=1.C([N:34]([CH:37]([CH3:39])[CH3:38])CC)(C)C.C1(N)CC1.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH2:24][CH2:25][CH2:26][CH2:27][F:28])[C:7]([CH2:9][N:10]3[C:14]4[CH:15]=[N:16][CH:17]=[CH:18][C:13]=4[N:12]([CH2:19][C:20]([NH:34][CH:37]4[CH2:39][CH2:38]4)=[O:21])[C:11]3=[O:23])=[N:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 67975407HCID 67975407, compoundHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium

Product 1

HCID 67975549HCID 67975549, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 100 ml dry flask, (3-{[5-chloro-1-(4-fluorobutyl)-1H-benzimidazol-2-yl]methyl}-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)acetic acid (P67, 300 mg, 0.69 mmol), diisopropylethylamine (0.29 mL, 2.08 mmol, 3 eq.), cyclopropylamine (60 μL, 0.83 mmol, 1.2 eq.) and 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium (HATU, 316.9 mg, 0.83 mmol, 1.2 eq.) were dissolved in DMF (50 mL). The solution was placed under N2 atmosphere and stirred at room temperature during 1 hour. The reaction mixture was diluted with water (20 ml) and extracted with dichloromethane (50 mL). The organic layer was dried with MgSO4 and evaporated. The residue was further crystallized in diisopropylether/acetonirile. The solid was filtered off and dried into the oven for 16 hours which gave 2-(3-{[5-chloro-1-(4-fluorobutyl)-1H-benzimidazol-2-yl]methyl}-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)-N-cyclopropylacetamide (P68, 86 mg, 26%) as a white solid; LCMS m/z=471 (M+H)+

Workup

  1. customIn a 100 ml dry flask
  2. extractionextracted with dichloromethane (50 mL)
  3. dry with materialThe organic layer was dried with MgSO4
  4. customevaporated
  5. customThe residue was further crystallized in diisopropylether/acetonirile
  6. filtrationThe solid was filtered off
  7. customdried into the oven for 16 hours which

Sources & evidence

ORD record
ord-542ffc1e64ec4852a182fe25a9e2443a
Source dataset
uspto-grants-2014_10
Patent number
US08865705B2

Reaction notes

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