Sodium Iodide → 5-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indazole-7-carboxamide

HRID 1888225Notes

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+].[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>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:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)(=[O:22])=[O:21])[CH2:16][CH2:15]1

Participants

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 (120 mg), sodium iodide (2 mg), and pyrrolidine (0.15 mL). The reaction mixture was heated to 60° C. for 2 hrs. 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 (40 mg, 46%)

Workup

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

Sources & evidence

ORD record: ord-70403dd19b794b63b8098329f9cbe9eb
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501780B2

Reaction notes

Loading…