Acetic Acid → HCID 57525642, compound

HRID 1594406Notes

Reaction equation

HRID 1594406 reaction equation
[C:1]([N:5]1[C:9]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]([CH:17]2[CH2:20][CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=3)[CH2:18]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[CH:33]1([NH2:36])[CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)[Cl:52]>>[ClH:52].[C:1]([N:5]1[C:9]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:13])[F:14])=[CH:8][C:7]([CH:17]2[CH2:18][CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][NH:36][CH:33]4[CH2:35][CH2:34]4)[CH:22]=3)[CH2:20]2)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57525641HCID 57525641, compound

Product 1

HCID 57525642HCID 57525642, compound

Procedure

To a stirring solution of N-{2-tert-butyl-5-[3-(3-formyl-phenyl)-cyclobutyl]-2H-pyrazol-3-yl}-2,2,2-trifluoro-acetamide (0.49 g, 1.25 mmol) in CH2Cl2 (13 mL) was added acetic acid (86 uL, 1.5 mmol), followed by cyclopropylamine (103 uL, 1.5 mmol). After 30 min, sodium triacetoxyborohydride (0.53 g, 2.5 mmol) was added. The reaction was quenched after four hr. with a saturated solution of NaHCO3. The aqueous layer was extracted with CH2Cl2, and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Formation of the hydrochloride salt was accomplished using 2M HCl in Et2O to give the title compound (0.53 g). This material was used without further purification.

Workup

  1. customThe reaction was quenched after four hr
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39167d1db4514bccb3706b001574cb9e
Source dataset
uspto-grants-2007_11
Patent number
US07300944B2

Reaction notes

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