HCID 25032952, compound → HCID 59321395, compound

HRID 1800831Notes

Reaction equation

HRID 1800831 reaction equation
[F:1][C:2]1[C:3]([C:22]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]2)=[O:23])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=2)=[N:11][CH:10]=1>ClCCl.FC(F)(F)C(O)=O>[F:1][C:2]1[C:3]([C:22]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:23])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=2)=[N:11][CH:10]=1

Participants

4

Reactant 1

HCID 25032952HCID 25032952, compound

Product 1

HCID 59321395HCID 59321395, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 4-((3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamido)methyl)piperidine-1-carboxylate (0.78 g, 1.40 mmol, described in Example 3) in dichloromethane (4 mL) and trifluoroacetic acid (4 mL) was stirred at 23° C. for 1 hour. The reaction was then concentrated to dryness and diluted with 10% water in acetonitrile+0.05% trifluoroacetic acid. This was purified on Preparative HPLC (acetonitrile/water/ammonium acetate) to give the title material (0.292 g, 45%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 1.12-1.23 (2H, m), 1.69 (2H, d, J=11.9 Hz), 2.31 (3H, s), 2.56-2.65 (2H, m), 3.08 (2H, d, J=12.4 Hz), 3.15 (2H, t, J=6.19 Hz), 6.86 (1H, d, J=5.31 Hz), 6.92 (1H, s), 7.06 (1H, t, J=5.31 Hz), 7.82 (1H, s), 8.17 (1H, d, J=5.30 Hz), 8.26 (1H, d, J=5.05 Hz), 8.74 (1H, t, J=6.06 Hz). LC/MS (M+H)+: 459. HPLC ret. time (Condition C): 3.333 min.

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. additiondiluted with 10% water in acetonitrile+0.05% trifluoroacetic acid
  3. customThis was purified on Preparative HPLC (acetonitrile/water/ammonium acetate)

Sources & evidence

ORD record
ord-cd4ba94973384bb4985010dcb32f58db
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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