Bromocyclopentane → HCID 59199106, compound

HRID 1913098Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]3[N:8]([N:12]=[C:13]([NH:15][C:16]4[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=4)[N:14]=3)[CH:9]=[CH:10][CH:11]=2)[CH:3]=[N:2]1.[CH:26]1(Br)[CH2:30][CH2:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[CH:26]1([N:1]2[CH:5]=[C:4]([C:6]3[C:7]4[N:8]([N:12]=[C:13]([NH:15][C:16]5[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=5)[N:14]=4)[CH:9]=[CH:10][CH:11]=3)[CH:3]=[N:2]2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of methyl 4-(8-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate (43 mg, 0.13 mmol, 1 equiv), cyclopentyl bromide (41 μL, 0.38 mmol, 3.0 equiv) and cesium carbonate (126 mg, 0.383 mmol, 3.0 equiv) in N,N-dimethylformamide (1 mL) was heated at 100° C. After 2 h, the reaction mixture was diluted with ethyl acetate, and the resulting solution was washed with saturated aqueous sodium chloride solution. The collected organic was concentrated. Purification of the resulting residue by flash column chromatography (20% ethyl acetate in dichloromethane) afforded a white solid (23.5 mg, 45% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.18 (s, 1 H), 8.74-8.55 (m, 2 H), 8.32 (s, 1 H), 7.91 (dd, J=13.9, 8.1 Hz, 3 H), 7.85 (d, J=8.9 Hz, 2 H), 7.10 (t, J=7.0 Hz, 1 H), 4.81 (s, 1 H), 3.82 (s, 3 H), 2.25-2.11 (m, 2), 2.11-1.93 (m, 2 H), 1.85 (d, J=3.5 Hz, 2 H), 1.77-1.63 (m, 2 H).

Workup

washthe resulting solution was washed with saturated aqueous sodium chloride solution
concentrationThe collected organic was concentrated
customPurification of the resulting residue by flash column chromatography (20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record: ord-88855f837d484d63aa7254abc539cd04
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609687B2

Reaction notes

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