Trimethylsilyl iodide → HCID 136374263, compound

HRID 601318Notes

Reaction equation

C([O:8][C:9]1[CH:38]=[CH:37][C:12]2[NH:13][C:14]([C:19]3[C:24](=[O:25])[N:23]([NH:26][CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[C:22]4[CH:33]=[CH:34][S:35][C:21]=4[C:20]=3[OH:36])=[N:15][S:16](=[O:18])(=[O:17])[C:11]=2[CH:10]=1)C1C=CC=CC=1.I[Si](C)(C)C>C(#N)C.O>[CH:27]1([NH:26][N:23]2[C:24](=[O:25])[C:19]([C:14]3[NH:13][C:12]4[CH:37]=[CH:38][C:9]([OH:8])=[CH:10][C:11]=4[S:16](=[O:18])(=[O:17])[N:15]=3)=[C:20]([OH:36])[C:21]3[S:35][CH:34]=[CH:33][C:22]2=3)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

Conditions

Temperature: 25 °C

Procedure

The product of Example 324D (0.114 g, 0.21 mmol) in dry acetonitrile (11 mL) at 25° C. was reacted with iodotrimethylsilane (0.29 mL, 2.1 mmol) at 50° C. for 4 hours. The reaction was cooled to 25° C. and diluted with water (50 mL). The resulting precipitate was collected by filtration and dried under reduced pressure to give the title compound (0.083 g, 87% yield). MS (ESI−) m/z 459 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.20 (m, 5 H) 1.66 (m, 5 H) 6.51 (s, 1 H) 7.18 (m, 2 H) 7.48 (d, J=5.52 Hz, 1 H) 7.57 (d, J=9.56 Hz, 1 H) 8.29 (d, J=5.15 Hz, 1 H) 10.42 (s, 1 H) 14.04 (s, 1 H) 14.93 (s, 1 H).

Workup

filtrationThe resulting precipitate was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-9187eaff509f4e8cae8f6a3de6d38bb6
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902203B2

Reaction notes

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