Diisopropylethylamine → HCID 68473102, compound

HRID 2064097Notes

Reaction equation

HRID 2064097 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:5]([C:7]([OH:9])=O)[N:6]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[C:48]([O:52][C:53](=[O:62])[NH:54][CH2:55][C@@H:56]1[CH2:61][CH2:60][CH2:59][CH2:58][NH:57]1)([CH3:51])([CH3:50])[CH3:49]>C(#N)C>[C:48]([O:52][C:53](=[O:62])[NH:54][CH2:55][C@@H:56]1[CH2:61][CH2:60][CH2:59][CH2:58][N:57]1[C:7]([C:5]1[N:6]=[C:2]([Br:1])[S:3][C:4]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:9])([CH3:51])([CH3:49])[CH3:50]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1501973tert-butyl N-{[(2S)-piperidin-2-yl]methyl}carbamateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 684742592-Bromo-5-(4-fluorophenyl)thiazole-4-carboxylic acid

Product 1

HCID 68473102HCID 68473102, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-bromo-5-(4-fluoro-phenyl)-thiazole-4-carboxylic acid (1.02 g, 3.38 mmol) was dissolved in acetonitrile (20 ml) followed by the addition of TBTU (1.19 g, 3.72 mmol) and DIPEA (547 mg, 4.22 mmol). Stirring was continued for 30 min. at rt. A solution of (S)-piperidin-2-ylmethyl-carbamic acid tert-butyl ester (725 mg, 3.38 mmol) in acetonitrile (20 ml) was added to the reaction mixture within 10 minutes and stiring was continued at rt for 24 h. The reaction mixture was concentrated under reduced pressure followed by the addition of aq. HCl (0.5 M, 50 ml). Stirring was continued for 30 min. The precipitated product was filtered off, washed with cold water and dried at HV to give the expected product (1.57 g). LC-MS: tR=1.03 min; [M+H]+=500.38.

Workup

  1. waitstiring was continued at rt for 24 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionfollowed by the addition of aq. HCl (0.5 M, 50 ml)
  4. stirringStirring
  5. waitwas continued for 30 min
  6. filtrationThe precipitated product was filtered off
  7. washwashed with cold water
  8. customdried at HV

Sources & evidence

ORD record
ord-3914d8327ed0414399d76edccb850f49
Source dataset
uspto-grants-2012_10
Patent number
US08288411B2

Reaction notes

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