HCID 136358423, compound → HCID 136358424, compound

HRID 601368Notes

Reaction equation

C([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][O:14][C:15]1[CH:43]=[CH:42][C:18]2[NH:19][C:20]([C:25]3[C:26](=[O:41])[N:27]([NH:36][CH2:37][CH:38]4[CH2:40][CH2:39]4)[C:28]4[C:33]([C:34]=3[OH:35])=[CH:32][CH:31]=[CH:30][CH:29]=4)=[N:21][S:22](=[O:24])(=[O:23])[C:17]=2[CH:16]=1)C1C=CC=CC=1>CN(C)C=O.[Pd]>[CH:38]1([CH2:37][NH:36][N:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:34]([OH:35])=[C:25]([C:20]3[NH:19][C:18]4[CH:42]=[CH:43][C:15]([O:14][CH2:13][C:9]5[NH:10][CH:11]=[CH:12][N:8]=5)=[CH:16][C:17]=4[S:22](=[O:23])(=[O:24])[N:21]=3)[C:26]2=[O:41])[CH2:40][CH2:39]1

Participants

Conditions

Temperature: 70 °C

Procedure

Product of Example 390A (16 mg, 0.027 mmol) in N,N-dimethylformamide (1 mL) was added 1,4-cyclodiene (25.5μl, 0.27 mmol) and palladium black (16 mg). The mixture was heated at 70° C. for 1 day. The mixture was filtered with Celite® and washed with N,N-dimethylformamide. The solution was evaporated under reduced pressure and the residue was chromatographed on silica gel eluting with dichloromethane:methanol (98:2) to give the title compound (6 mg, 44%). 1H NMR (300 MHz, DMSO-d6) δ 0.16 (d, J=4.41 Hz, 2 H) 0.43 (d, J=7.35 Hz, 2 H) 0.99 (m, 1 H) 2.78 (s, br, 2 H) 5.25 (s, 2 H) 6.27 (s, br, 1 H) 7.22 (s, 2 H) 7.31 (m, 1 H) 7.39 (dd, J=9.01, 2.76 Hz, 1 H) 7.49 (d, J=2.57 Hz, 1 H) 7.54 (d, J=8.82 Hz, 1 H) 7.77 (m, 1 H) 7.95 (d, J=8.09 Hz, 1 H) 8.13 (dd, J=8.09 Hz, 1.47 Hz, 1 H) 14.83 (s, br, 1 H). MS (ESI−) m/z 505 (M−H)−.

Workup

filtrationThe mixture was filtered with Celite®
washwashed with N,N-dimethylformamide
customThe solution was evaporated under reduced pressure
customthe residue was chromatographed on silica gel eluting with dichloromethane:methanol (98:2)

Sources & evidence

ORD record: ord-c58f30b5455f4d26ac10ca49f8919448
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902203B2

Reaction notes

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