Piperidine → HCID 67122939, compound

HRID 2046413Notes

Reaction equation

HRID 2046413 reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]3[CH2:23][CH2:22][CH2:21][C:20]([F:25])([F:24])[C@@H:19]3[NH:26][C:27]([C:29]3[S:30][C:31]([CH2:43][CH3:44])=[C:32]([C:34]4[N:38]5[N:39]=[CH:40][CH:41]=[CH:42][C:37]5=[N:36][CH:35]=4)[CH:33]=3)=[O:28])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[NH2:17][C@@H:18]1[C@@H:19]([NH:26][C:27]([C:29]2[S:30][C:31]([CH2:43][CH3:44])=[C:32]([C:34]3[N:38]4[N:39]=[CH:40][CH:41]=[CH:42][C:37]4=[N:36][CH:35]=3)[CH:33]=2)=[O:28])[C:20]([F:25])([F:24])[CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 68754973HCID 68754973, compound

Product 1

HCID 67122939HCID 67122939, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9H-Fluoren-9-ylmethyl[(1S,2R)-2-({[5-ethyl-4-(imidazo[1,2-b]pyridazin-3-yl)thiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexyl]carbamate (168 mg, 0.268 mmol) was dissolved in DMF (2.68 mL) and piperidine added (0.265 mL, 2.68 mmol). The solution was stirred at room temperature for 2 h. The solution was then subjected to prep HPLC for purification. The compound was neutralized by taking the fractions and adding an aqueous saturated sodium bicarbonate solution and extracting three times with dichloromethane. The combined organics were dried with magnesium sulfate, filtered, and concentrated to afford the title compound as a yellow solid. 1H NMR (500 MHz, CD3SOCD3) δ 8.61 (d, 1H); 8.41 (d, 1H); 8.21 (d, 1H); 8.19 (s, 1H); 7.95 (s, 1H); 7.29 (dd, 1H); 4.07 (m, 1H); 2.86 (m, 1H); 2.85 (q, 2H); 2.07 (m, 1H); 1.88 (m, 1H); 1.86 (m, 1H); 1.70 (m, 1H); 1.36 (m, 2H); 1.21 (t, 3H). LRMS (APCI) calc'd for (C19H21F2N5OS) [MA-1]+, 406.1. found 406.1.

Workup

  1. customfor purification
  2. additionadding an aqueous saturated sodium bicarbonate solution
  3. extractionextracting three times with dichloromethane
  4. dry with materialThe combined organics were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0286418522a146b2a81b4caeac9f83a0
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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