Dimethylamine → HCID 178483611, compound

HRID 1888210Notes

Reaction equation

HRID 1888210 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][CH2:25]Cl)(=[O:22])=[O:21])[CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].[CH3:35][NH:36][CH3:37]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][CH2:25][N:36]([CH3:37])[CH3:35])(=[O:22])=[O:21])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 178513508HCID 178513508, compound2×

Product 1

HCID 178483611HCID 178483611, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indazole-7-carboxamide (Intermediate 7) (200 mg, 0.432 mmol) in DMF (5 mL) was added K2CO3 (250 mg), sodium iodide (10 mg), and 2M dimethyl amine in DMF (1 mL) The reaction mixture was heated to 60° C. overnight. The solution was filtered. The filtrate was purified by using a Gilson semi-preparative HPLC system with a YMC ODS-A (C-18) column 50 mm by 20 mm ID, eluting with 40% B to 80% B in 3.2 min, hold for 1 min where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to afford the title compound (100 mg, 49%)

Workup

  1. filtrationThe solution was filtered
  2. customThe filtrate was purified
  3. washeluting with 40% B to 80% B in 3.2 min

Sources & evidence

ORD record
ord-401995e94f214ce8886d185f5220a586
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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