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Water → HCID 68698709, compound

HRID 1990884
Notes
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Reaction equation

HRID 1990884 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:25]1([C:29](Cl)=[O:30])[CH2:28][CH2:27][CH2:26]1.C(N(C(C)C)CC)(C)C.O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([NH:24][C:29]([CH:25]4[CH2:28][CH2:27][CH2:26]4)=[O:30])=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 78705Cyclobutanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 68695194HCID 68695194, compound

Product 1

HCID 68698709HCID 68698709, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 4-(5-amino-benzooxazol-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.40 g, 4.21 mmol, 1.0 equiv) in anhydrous DMF (5 mL) was added cyclobutanecarbonyl chloride (0.55 g, 4.63 mmol, 1.1 equiv; commercially available) and diisopropylethylamine (1.03 mL, 1.14 g, 8.84 mmol, 2.1 equiv) and the reaction mixture stirred at rt. After 1 h, water was added (50 mL) and the water phase extracted with dichloromethane (3×50 mL). The combined organic phases were dried over MgSO4, the organic solvent removed under reduced pressure and the crude oil purified with column chromatography on silica eluting with ethyl acetate/heptane (2:1) to afford 1.1 g (64%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.46-1.50 (m, 2H), 1.47 (s, 9H), 1.94-2.02 (m, 2H), 2.10-2.13 (m, 2H), 2.20-2.26 (m, 2H), 2.34-2.47 (m, 2H), 2.95-2.97 (m, 2H), 3.10-3.22 (m, 1H), 3.90 (br s, 1H), 4.05 (br s, 2H), 5.24 (brs, 1H), 7.14 (d, J=8.6 Hz, 1H), 7.28 (brs, 1H), 7.33 (d, J=8.6 Hz, 1H), 7.41 (brs, 1H). 13C NMR (75 MHz, CDCl3): δ 18.05, 25.33, 28.41, 32.30, 40.85, 42.49, 50.45, 79.76, 108.41, 108.54, 113.47, 134.57, 143.38, 145.21, 154.70, 161.76, 173.04. MS (ISP): 413.1 [M−H]−.

Workup

  1. extractionthe water phase extracted with dichloromethane (3×50 mL)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe organic solvent removed under reduced pressure
  4. customthe crude oil purified with column chromatography on silica eluting with ethyl acetate/heptane (2:1)

Sources & evidence

ORD record
ord-739800feb7b04216aeb41dd4b7c8a3e6
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07645753B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes