HCID 59394234, compound → HCID 59394262, compound

HRID 1887609Notes

Reaction equation

HRID 1887609 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20][C:21]4[N:26]=[CH:25][N:24]=[C:23]([CH2:27][N:28]5[CH2:33][CH2:32][CH:31]([C:34]([O:36]C)=[O:35])[CH2:30][CH2:29]5)[CH:22]=4)=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)=[O:10])=[CH:4][C:3]=1[C:38]([F:41])([F:40])[F:39]>C1COCC1.O.[Li+].[OH-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20][C:21]4[N:26]=[CH:25][N:24]=[C:23]([CH2:27][N:28]5[CH2:33][CH2:32][CH:31]([C:34]([OH:36])=[O:35])[CH2:30][CH2:29]5)[CH:22]=4)=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)=[O:10])=[CH:4][C:3]=1[C:38]([F:41])([F:39])[F:40]

Participants

4

Reactant 1

HCID 59394234HCID 59394234, compound

Product 1

HCID 59394262HCID 59394262, compound

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl 1-((6-(1-(4-fluoro-3-(trifluoromethyl)phenylcarbamoyl)-1H-indol-5-yloxy)pyrimidin-4-yl)methyl)piperidine-4-carboxylate (0.13 g, 0.228 mmol) in 40 mL of THF/H2O (3:1), 2 M aq LiOH solution (0.23 mL) is added. The mixture is stirred at rt for 3.5 h before being concentrated and purified by semi-prep HPLC (12-48% CAN/H2O with 0.1% TFA) to give the title compound. MS (ESI) m/z 558.1 (M+1); 1H NMR (400 MHz, DMSO-d5) δ ppm 10.43 (s, 1H), 9.93-10.12 (m, 1H), 8.88 (s, 1H), 8.32 (d, J=9.1 Hz, 1H), 8.08-8.17 (m, 2H), 7.96-8.06 (m, 1H), 7.58 (t, J=9.9 Hz, 1H), 7.52 (d, J=2.5 Hz, 1H), 7.25 (br. S., 1H), 7.17 (dd, J=9.0, 2.4 Hz, 1H), 6.83 (d, J=3.5 Hz, 1H), 4.39-4.60 (m, 2H), 3.45-3.57 (m, 2H), 2.98-3.17 (m, 2H), 1.95-2.14 (m, 3H), 1.73-1.91 (m, 2H)

Workup

  1. concentrationbefore being concentrated
  2. custompurified by semi-prep HPLC (12-48% CAN/H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-fd27620c59ec474c84e46fe2879b045d
Source dataset
uspto-grants-2013_08
Patent number
US08501756B2

Reaction notes

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