Sodium Iodide → 5-Azepan-1-yl-pentanoic acid (5-pyridin-4-yl-1H-pyrazol-3-yl)-amide

HRID 1695220Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[N:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:19][N:18]=[C:17]([NH2:20])[CH:16]=2)=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C.[NH:30]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.[Na+].[I-]>CC(N(C)C)=O>[N:9]1[CH:10]=[CH:11][C:12]([C:15]2[NH:19][N:18]=[C:17]([NH:20][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][N:30]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:16]=2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The product was prepared according to the general synthetic method for the one-pot synthesis of ω-amino-alkanoic acid (1H-pyrazol-3-yl-5-aryl)-amides. A solution of 5-bromovaleryl chloride (0.125 mL, 0.94 mmol) in dry DMA (1 mL) was cooled to −10° C. (ice/water bath) under N2; 5-Pyridin-4-yl-1H-pyrazol-3-ylamine (151 mg, 0.94 mmol) and diisopropylethylamine (0.324 mL, 1.88 mmol) in dry DMA (1 ml) were added. The reaction was left stirring for 1 h at 0° C. and then azepane (0.265 mL, 2.35 mmol) and NaI (0.94 mmol, 1 eq) were added.

Workup

customThe product was prepared
waitThe reaction was left

Sources & evidence

ORD record: ord-245717ad71e94d109a97bf6ddb366a23
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163729B2

Reaction notes

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