12-Aminododecanoic Acid → HCID 178512403, compound

HRID 2420746Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].C(N(C(C)C)CC)(C)C.I.[NH2:26][C:27]1[C:28]([C:35]([NH:37][C:38](=[NH:41])SC)=[O:36])=[N:29][C:30]([Cl:34])=[C:31]([NH2:33])[N:32]=1>C(O)C>[NH2:26][C:27]1[C:28]([C:35]([N:37]=[C:38]([NH2:41])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:36])=[N:29][C:30]([Cl:34])=[C:31]([NH2:33])[N:32]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 12-aminododecanoic acid (1) (0.096 g, 0.45 mmol) and diisopropylethylamine (0.39 mL, 2.23 mmol) in absolute ethanol (5 mL) was stirred at 70° C. for 30 min. 1-(3,5-Diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (191 mg, 0.49 mmol) was added in one portion and heating at 70° C. was continued for a further 16 hours. After this time, the reaction was cooled to room and the resulting yellow precipitate collected by filtration and washed with ethanol (2×2 mL). Further purification by Biotage silica gel column chromatography using a gradient of 3% to 20% of 10% concentrated aqueous ammonium hydroxide in methanol to dichloromethane afforded acid 2 (96 mg, 50%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 1.25 (m, 14H), 1.50 (m, 4H), 2.18 (t, 2H), 3.15 (t, 2H), 6.92 (m, 3H). m/z (ESI) 428 [C18H30ClN7O3+H]+. mp 194-196° C.

Workup

temperatureAfter this time, the reaction was cooled to room
filtrationthe resulting yellow precipitate collected by filtration
washwashed with ethanol (2×2 mL)
customFurther purification by Biotage silica gel column chromatography

Sources & evidence

ORD record: ord-23062a45966f4b0c83f3c8e0ad9a1b85
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956059B2

Reaction notes

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