Sodium Iodide → HCID 10007400, compound

HRID 1453787Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11].C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:46]=[CH:45][C:22]([CH2:23][N:24]([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[C:25](=[O:38])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[CH:29][CH:28]=2)=[CH:21][CH:20]=1.[I-].[Na+]>CN(C=O)C>[F:18][C:19]1[CH:46]=[CH:45][C:22]([CH2:23][N:24]([CH:39]2[CH2:44][CH2:43][N:42]([CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][CH2:8][CH2:7][C:6]3=[O:11])[CH2:41][CH2:40]2)[C:25](=[O:38])[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[CH:31][CH:32]=2)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 48 °C

Procedure

A solution of 1-(3-chloropropyl)piperidin-2-one (32 mg, 0.18 mmol) in dry DMF (2 mL) was added to a suspension of potassium carbonate (52 mg, 0.38 mmol) and N-(4-fluorobenzyl)-2-(4-isobutoxyphenyl)-N-piperidin-4-yl-acetamide 103NLS56 (62 mg, 0.15 mmol) in dry DMF (2 mL). After addition of sodium iodide (25 mg, 0.17 mmol) the mixture was stirred overnight at 48° C. Afterwards it was partitioned between water and dichloromethane. The organic layer were dried over sodium sulphate, filtered and evaporated to dryness. Purification of the residue by reversed phase HPLC (C18) afforded the desired compound (2.6 mg, 3%).

Workup

customAfterwards it was partitioned between water and dichloromethane
dry with materialThe organic layer were dried over sodium sulphate
filtrationfiltered
customevaporated to dryness
customPurification of the residue by reversed phase HPLC (C18)

Sources & evidence

ORD record: ord-85b51fa1c07b4db299ecf403420b6b22
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476682B2

Reaction notes

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