HCID 89434881, compound → HCID 89434974, compound

HRID 1776927Notes

Reaction equation

HRID 1776927 reaction equation
[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:39]([CH2:44][C:45]6[CH:50]=[CH:49][C:48]([B:51]7[O:55]C(C)(C)C(C)(C)[O:52]7)=[CH:47][CH:46]=6)[S:40]([CH3:43])(=[O:42])=[O:41])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=7)=[C:24]([C:34]([NH:36][CH3:37])=[O:35])[C:23]=6[CH:38]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1>C1COCC1.O>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:39]([CH2:44][C:45]6[CH:46]=[CH:47][C:48]([B:51]([OH:55])[OH:52])=[CH:49][CH:50]=6)[S:40]([CH3:43])(=[O:41])=[O:42])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=7)=[C:24]([C:34](=[O:35])[NH:36][CH3:37])[C:23]=6[CH:38]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 89434881HCID 89434881, compound

Product 1

HCID 89434974HCID 89434974, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)methylsulfonamido)benzofuran-3-carboxamide (0.12 g, 0.15 mmol) and NaIO4 (0.16 g, 0.74 mmol) in THF/H2O (12 mL/4 mL) was stirred at room temperature for 24 hours. The mixture was filtered and extracted by EtOAc. The combined organic phases was washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-HPLC to provide Compound 205. 1H-NMR (Methanol-d4, 400 MHz) δ 8.00 (s, 2H), 7.77˜7.79 (m, 2H), 7.53˜7.66 (m, 1H), 7.51˜7.52 (m, 1H), 7.22˜7.44 (m, 6H), 7.11˜7.14 (m, 1H), 6.99˜7.01 (m, 1H), 6.91˜6.93 (m, 1H), 6.82˜6.86 (m, 1H), 6.14 (s, 2H), 4.84˜4.86 (m, 1H), 4.50˜4.58 (m, 1H), 3.17˜3.20 (m, 3H), 2.93 (s, 3H). MS (M+H)+: 735.

Workup

  1. filtrationThe mixture was filtered
  2. extractionextracted by EtOAc
  3. washThe combined organic phases was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-1737578bb852485685a97c91c5bbb890
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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