Diisopropylethylamine → (R)-3-[(6-methyl-imidazo[2,1-b]thiazole-5-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1094256Notes

Reaction equation

HRID 1094256 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[CH3:15][C:16]1[N:17]=[C:18]2[N:22]([C:23]=1[C:24](O)=[O:25])[CH:21]=[CH:20][S:19]2.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.CC(=O)OCC.CCCCCCC>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([NH:1][C:24]([C:23]2[N:22]3[C:18]([S:19][CH:20]=[CH:21]3)=[N:17][C:16]=2[CH3:15])=[O:25])[CH2:3]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 3299796-Methylimidazo[2,1-B][1,3]thiazole-5-carboxylic acidHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 2724699PyBOP

Product 1

HCID 66639536(R)-3-[(6-methyl-imidazo[2,1-b]thiazole-5-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl esterYield 101%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×HCID 21899848Ethylacetate heptaneSolvent

Procedure

A mixture of (R)-3-amino-1-N-Boc-piperidine (800 mg), 6-methyl-imidazo[2,1-b]thiazole-5-carboxylic acid (801.5 mg), PyBOP (2.08 g), DIEA (1.57 mL) in dry DMF (10 mL) was stirred at RT under nitrogen for 20 h. The reaction mixture was diluted with EA, washed with water. The aqueous phase was extracted twice with EA, the combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to yield a crude light brown oil. FC (EA/n-heptane: 1/1 to EA) gave 1.47 g (100%) of the title compound as a solid.

Workup

  1. washwashed with water
  2. extractionThe aqueous phase was extracted twice with EA
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude light brown oil

Sources & evidence

ORD record
ord-b882a0954af241758a0608287c0273ca
Source dataset
uspto-grants-2012_03
Patent number
US08133901B2

Reaction notes

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