Cyclopropanemethanamine → HCID 57444438, compound

HRID 577774Notes

Reaction equation

HRID 577774 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[C:17]2[C:24]([CH3:25])=[N:23][N:22]([CH3:26])[C:18]2=[N:19][C:20]=1Cl)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.CC(C)([O-])C.[K+].[CH:42]1([CH2:45][NH2:46])[CH2:44][CH2:43]1>CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[C:17]2[C:24]([CH3:25])=[N:23][N:22]([CH3:26])[C:18]2=[N:19][C:20]=1[NH:46][CH2:45][CH:42]1[CH2:44][CH2:43]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

7

Reactant 3

HCID 75646CyclopropanemethanamineHCID 23665647Potassium tert-butoxideHCID 57486811HCID 57486811, compound

Product 1

HCID 57444438HCID 57444438, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3,5-bis-trifluoromethyl-benzyl)-(6-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-ylmethyl)-(2-methyl-2H-tetrazol-5-yl)-amine (0.5 g, 0.9 mmol), potassium tertiary butoxide (0.43 g, 3 mmol), cyclopropylmethyl amine (0.275 g, 3 mmol), and Pd(OAc)2 (0.01 g, 0.004 mmol), BINAP (0.03 g, 0.04 mmol) was prepared in a 10 mL pressure vial. The pressure vial was placed in the focused microwave oven (CEM Discovery) and irradiated for 20 min at 110° C. by using 250 Watt microwave power. After this mixture was cooled to RT, ethyl acetate (100 mL) was added to the vial. The organic layer was washed with water (3×100 mL) and dried and concentrated. The resultant oil was purified by column chromatography using silica gel (230-400 mesh) and eluting the column with 10% ethyl acetate in hexane afforded a colorless solid (0.485 g), yield: 90%.

Workup

  1. customwas prepared in a 10 mL pressure vial
  2. customirradiated for 20 min at 110° C.
  3. washThe organic layer was washed with water (3×100 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe resultant oil was purified by column chromatography
  7. washeluting the column with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6acea268396342fbbbb925ccbbcf5057
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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