HCID 117874814, compound → {1-[5-({3-[(1R)-1-aminopropyl]-6-chloro-2-fluorophenyl}carbonyl)pyridin-2-yl]-1H-pyrazol-4-yl}methanol

HRID 2283401Notes

Reaction equation

HRID 2283401 reaction equation
[NH2:1][C@@H:2]([C:5]1[C:6]([F:30])=[C:7]([C:12]([C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH:24]=[C:23]([C:25](OCC)=[O:26])[CH:22]=[N:21]3)=[N:18][CH:19]=2)=[O:13])[C:8]([Cl:11])=[CH:9][CH:10]=1)[CH2:3][CH3:4].CC(C[AlH]CC(C)C)C.C1COCC1>C1COCC1>[NH2:1][C@@H:2]([C:5]1[C:6]([F:30])=[C:7]([C:12]([C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH:24]=[C:23]([CH2:25][OH:26])[CH:22]=[N:21]3)=[N:18][CH:19]=2)=[O:13])[C:8]([Cl:11])=[CH:9][CH:10]=1)[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 117874814HCID 117874814, compoundHCID 131729343Dibal-H thf2×

Product 1

HCID 89545008{1-[5-({3-[(1R)-1-aminopropyl]-6-chloro-2-fluorophenyl}carbonyl)pyridin-2-yl]-1H-pyrazol-4-yl}methanolYield 10.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To ethyl 1-[5-({3-[(1R)-1-aminopropyl]-6-chloro-2-fluorophenyl}carbonyl)pyridin-2-yl]-1H-pyrazole-4-carboxylate (Example 41) (0.154 g, 0.358 mmol) in THF (4 ml) at 0° C. was added 1M DiBAL-H/THF (0.78 ml, 0.787 mmol) stirred at 0° C. for 15 minutes allowed to warm to ambient, further 1M DiBAL-H/THF (0.78 ml, 0.787 mmol) added left further 30 minutes at ambient. Reaction quenched with Rochelles salt and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated, purified by Prep HPLC to give {1-[5-({3-[(1R)-1-aminopropyl]-6-chloro-2-fluorophenyl}carbonyl)pyridin-2-yl]-1H-pyrazol-4-yl}methanol (0.015 g).

Workup

  1. temperatureto warm
  2. waitleft further 30 minutes at ambient
  3. customReaction
  4. customquenched with Rochelles salt
  5. extractionextracted with EtOAc
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by Prep HPLC

Sources & evidence

ORD record
ord-e777b9222d1d42538b63c869b45ea75a
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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