Lithium iodide → HCID 11649022, compound

HRID 1725978Notes

Reaction equation

N[C:2]1[CH:7]=[CH:6]C=C[C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[C:22]([O:24]C)=[O:23])(=[O:10])=[O:9].[C:26]([N:33]1[CH:37]=[CH:36]N=C1)([N:28]1[CH:32]=[CH:31]N=C1)=[O:27].NCC[CH:41]1[CH2:45][CH2:44][CH2:43][N:42]1[CH3:46].[Li+].[I-]>C1COCC1>[CH3:46][N:42]1[CH2:41][CH2:45][CH2:44][CH:43]1[CH2:36][CH2:37][NH:33][C:26]([NH:28][C:32]1[CH:31]=[CH:6][CH:7]=[CH:2][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[C:22]([OH:24])=[O:23])(=[O:9])=[O:10])=[O:27]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of Example 418C (145.6 mg, 0.404 mmol) in THF (0.25 mL) was treated with carbonyldiimidazole (65.5 mg, 0.404 mmol), heated to 50° C. for 1.5 hours, cooled to room temperature, treated with 2-(2-aminoethyl)-1-methylpyrrolidine. (58 μL, 0.404 mmol), stirred for 24 hours, and concentrated. The residue was dissolved in pyridine (0.5 mL), treated with LiI (162.2 mg, 1.212 mmol), heated in a microwave reactor at 150° C. for 25 minutes, concentrated, and purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product. (58.7 mg, 29%). MS (ESI(−)) m/e 499 (M−H)-; 1H NMR (300 MHz, DMSO-d6) δ 9.74 (s, 1H), 8.21 (m, 1H), 7.66 (dd, 1H), 7.53 (ddd, 1H), 7.32 (t, 1H), 7.07 (td, 1H), 6.96 (d, 1H), 6.53 (d, 1H), 3.18 (m, 3H), 3.01 (m, 2H), 2.78 (s, 3H), 2.66 (m, 4H), 2.30 (m, 2H), 1.92 (m, 2H), 1.67 (m, 4H), 1.28 (m, 1H), 0.87 (m, 1H).

Workup

temperaturecooled to room temperature
concentrationconcentrated
dissolutionThe residue was dissolved in pyridine (0.5 mL)
temperatureheated in a microwave reactor at 150° C. for 25 minutes
concentrationconcentrated
custompurified by C18 reverse-phase

Sources & evidence

ORD record: ord-80c7a6aad8624666912bf5d109d751e8
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491718B2

Reaction notes

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