Triethylamine → HCID 178513546, compound

HRID 1888257Notes

Reaction equation

HRID 1888257 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][N:12]=[C:11]3[CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:27][CH2:28][S:29](Cl)(=[O:31])=[O:30].[CH2:33]([N:35](CC)[CH2:36][CH3:37])[CH3:34].C([O-])([O-])=O.[K+].[K+].N1CCCC1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][N:12]=[C:11]3[CH:20]2[CH2:25][CH2:24][N:23]([S:29]([CH2:28][CH2:27][N:35]3[CH2:36][CH2:37][CH2:34][CH2:33]3)(=[O:31])=[O:30])[CH2:22][CH2:21]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 31268PyrrolidineHCID 1785135395-(3-fluorophenyl)-3-(4-piperidinyl)-1H-indazole-7-carboxamide2×

Product 1

HCID 178513546HCID 178513546, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

This compound was prepared in a fashion analogous to the procedure described in Example 16. Thus, 5-(3-fluorophenyl)-3-(4-piperidinyl)-1H-indazole-7-carboxamide (Intermediate 15) (75 mg, 0.167 mmol) was reacted with 2-chloro-1-ethanesulfonyl chloride (17 uL, 0.167 mmol) in the presence of triethyl amine (93 uL, 0.665 mmol) in DMF (2 mL) at 0° C. After 10 mins, K2CO3 (46 mg, 0.334 mmol) and pyrrolidine (41 uL, 0.501 mmol) were added. The reaction mixture was heated to 100° C. overnight. The resulting suspension was filtered. The filtrate was concentrated and the residue was purified by using a Gilson semi-preparative HPLC system, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to afford the title compound (12.6 mg, 15% for 2 steps).

Workup

  1. customThis compound was prepared in a fashion analogous to the procedure
  2. filtrationThe resulting suspension was filtered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified
  5. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-9388ba3fc1e34a3cb74be1b53e71615f
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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