Acetic Acid → HCID 11249049, compound

HRID 1825841Notes

Reaction equation

HRID 1825841 reaction equation
O=[CH:2][CH2:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[O:16])[CH:10]=[CH:11]2)=[N:6]1.CC(O)=O.[NH:35]1[CH2:40][CH2:39][CH2:38][CH:37]([CH2:41][OH:42])[CH2:36]1>CO>[OH:42][CH2:41][CH:37]1[CH2:38][CH2:39][CH2:40][N:35]([CH2:2][CH2:3][CH2:4][N:5]2[CH:13]=[C:12]3[C:7]([CH:8]=[C:9]([NH:14][C:15]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[CH:20][CH:19]=4)=[O:16])[CH:10]=[CH:11]3)=[N:6]2)[CH2:36]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 107308Piperidin-3-ylmethanolHCID 221389081-[2-(3-oxopropyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea

Product 1

HCID 11249049HCID 11249049, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[2-(3-oxopropyl)-2H-indazol-6-yl]-3-(4-phenoxyphenyl)urea (20 mg, 0.05 mmol) in Methanol containing 2% v/v AcOH (1 mL) was added 3-piperidinemethanol (10 mg, 0.10 mmol) and MS-CNBH3 (52 mg, 0.065 mmol). The reaction was shaken vigorously at 40 C for 18h. The reaction was filtered, eluting with additional Methanol (3×0.5 mL). The sample was directly purified by RP-HPLC to afford the titled product. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.15 (m, 1 H), 1.65 (m, 2 H), 1.83 (m, 2 H), 2.30 (m, 2 H), 2.63 (m, 1 H), 2.77 (m, 1 H), 3.10 (m, 2 H), 3.24 (dd, J=10.68, 6.61 Hz, 1 H), 3.36 (m, 1 H), 3.44 (m, 2 H), 4.47 (t, J=6.27 Hz, 2 H), 6.97 (m, 5 H), 7.09 (m, 1 H), 7.36 (m, 2 H), 7.49 (m, 2 H), 7.62 (m, 1 H), 7.90 (s, 1 H), 8.29 (s, 1 H), 8.76 (m, 2 H) and 9.16 (s, 1 H); MS (ESI) 500 (M+H)+.

Workup

  1. filtrationThe reaction was filtered
  2. washeluting with additional Methanol (3×0.5 mL)
  3. customThe sample was directly purified by RP-HPLC

Sources & evidence

ORD record
ord-0a2bbc9689dd4df0ae201b9f3ebc0503
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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