4-[4-Amino-5-(3-fluorobenzoyl)thiazol-2-ylamino]piperidine-1-carboxylic acid tert-butyl ester → HCID 11951611, compound

HRID 30155Notes

Reaction equation

HRID 30155 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][C:17]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)=[C:18]([NH2:20])[N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[NH2:20][C:18]1[N:19]=[C:15]([NH:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[S:16][C:17]=1[C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)=[O:29]

Participants

4

Reactant 1

HCID 119514404-[4-Amino-5-(3-fluorobenzoyl)thiazol-2-ylamino]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11951611HCID 11951611, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-[4-Amino-5-(3-fluorobenzoyl)thiazol-2-ylamino]piperidine-1-carboxylic acid tert-butyl ester (0.82 g, 1.95 mmol) (Example 3) was dissolved in a mixture of trifluoroacetic acid (16 mL) and methylene chloride (30 mL). After 1 hr, all solvent was removed and the residue dissolved in methylene chloride (300 mL). This was washed with 10% Na2CO3 (50 mL), dried (Na2SO4) and concentrated to give a semi solid. This was triturated with ethyl ether and filtered to give 450 mg (72% yield) of [4-amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluorophenyl)methanone. 1H NMR (DMSO−d6, 300 MHz) δ1.38 (m, 2H, CH2), 1.88 (m, 2H, CH2), 2.95 (m, 2H, CH2), 3.32 (brd, 2H, CH2), 3.6-4.0 (broad, 1H, CH), 3.78 (s, 3H, OCH3), 7.31 (t, 1H, Aromatic), 7.38 (d, 1H, Aromatic), 7.48 (t, 1H, Aromatic), 7.51 (q, 1H, Aromatic), 8.01 (brd, 1H, NH), 8.48 (brd, 1H, NH), 8.70 (brd, 1H, NH). LR-MS-ES(±): Compatible with 320 MW.

Workup

  1. customall solvent was removed
  2. dissolutionthe residue dissolved in methylene chloride (300 mL)
  3. washThis was washed with 10% Na2CO3 (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a semi solid
  7. customThis was triturated with ethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-9a6311fa38b04eaf914d9afd0888cc10
Source dataset
uspto-grants-2008_09
Patent number
US07423053B2

Reaction notes

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