Sodium Iodide → HCID 178513531, compound

HRID 1888287Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:21]=3)[NH:16][N:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].C([O-])([O-])=O.[K+].[K+].[OH:38][CH:39]1[CH2:44][CH2:43][CH:42]([NH2:45])[CH2:41][CH2:40]1.[I-].[Na+]>CN(C=O)C>[OH:38][CH:39]1[CH2:44][CH2:43][CH:42]([NH:45][CH2:2][CH2:3][CH2:4][S:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[C:22]4[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH:21]=4)[NH:16][N:15]=3)[CH2:10][CH2:9]2)(=[O:7])=[O:6])[CH2:41][CH2:40]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indazole-7-carboxamide (Intermediate 22) (19 mg, 0.0413 mmol) in DMF (1 mL) was added K2CO3 (25 mg, 0.165 mmol), 4-hydroxycyclohexylamine (33 mg, 0.2065 mmol) and sodium iodide (1.0 mg). The reaction mixture was heated to 120° C. for 14 hrs. The solution was filtered and concentrated. The residue 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 10% B to 80% B in 10 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 (12.2 mg, 55%).

Workup

filtrationThe solution was filtered
concentrationconcentrated
customThe residue was purified
washeluting with 10% B to 80% B in 10 min

Sources & evidence

ORD record: ord-e308cd1ac7374f3aa1fde70b10ee3964
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501780B2

Reaction notes

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