Iodine → HCID 178521006, compound

HRID 931252Notes

Reaction equation

[N:1]1([C:6]([C@@H:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]3[N:19]=[C:18]4[NH:20][C:21]([C:23]5[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=5)[C:26]#[N:27])=[N:22][C:17]4=[CH:16][CH:15]=3)[CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N-:31]=[N+:32]=[N-:33].[Na+].II>CN(C)C=O>[N:27]1[NH:31][N:32]=[N:33][C:26]=1[C:25]1[CH:24]=[C:23]([C:21]2[NH:20][C:18]3=[N:19][C:14]([N:10]4[CH2:11][CH2:12][CH2:13][C@@H:8]([C:6]([N:1]5[CH2:2][CH2:3][CH2:4][CH2:5]5)=[O:7])[CH2:9]4)=[CH:15][CH:16]=[C:17]3[N:22]=2)[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (R)-3-(5-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzonitrile (30 mg, 0.07 mmol) in N,N-dimethylformamide (2 mL) were added sodium azide (6 mg, 0.09 mmol) and iodine (3 mg). The reaction mixture was heated for 12 h at 120° C., then was cooled. The mixture was filtered, and the filtrate was concentrated. The resulting residue was triturated with diethyl ether to afford (R)-(1-(2-(3-(2H-tetrazol-5-yl)phenyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone as yellow solid (36 mg, 92%). MS (ES+APCI) (M+H) 444.1; HPLC retention time 3.551 min (Method C1). 1H NMR (400 MHz, DMSO-d6) δ 1.50-2.00 (m, 8H), 2.60-2.68 (m, 1H), 2.83-2.97 (m, 3H), 3.25-3.31 (m, 1H), 3.42-3.50 (m, 1H), 3.52-3.60 (m, 1H), 4.32 (d, 1H), 4.42 (d, 1H), 6.83 (d, 1H), 7.47 (t, 1H), 7.81 (d, 1H), 7.94-8.02 (m, 2H), 8.79 (s, 1H), 13.02 (s, 1H).

Workup

temperaturewas cooled
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated
customThe resulting residue was triturated with diethyl ether

Sources & evidence

ORD record: ord-018656d87e20427ca5a9f15ace8e64c9
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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