Ammonia → HCID 86707936, compound

HRID 2400279Notes

Reaction equation

HRID 2400279 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:22]3[CH:26]=[CH:25][S:24][CH:23]=3)[N:8]2[CH2:11][C:12]2[N:17]=[C:16]([C:18]([O:20]C)=O)[CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[O:27][CH3:28].[NH3:29]>O1CCCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:22]3[CH:26]=[CH:25][S:24][CH:23]=3)[N:8]2[CH2:11][C:12]2[N:17]=[C:16]([C:18]([NH2:29])=[O:20])[CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[O:27][CH3:28]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86707937HCID 86707937, compound

Product 1

HCID 86707936HCID 86707936, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 6-[6-fluoro-5-methoxy-2-(thiophen-3-yl)indol-1-ylmethyl]pyridine-2-carboxylate (168 mg) and ammonia (about 7 mol/L methanol solution, 4.2 mL) was stirred at room temperature for 6 hours. The reaction mixture was diluted with tetrahydrofuran (4.2 mL), followed by stirring for 66 more hours. The reaction mixture was then concentrated under reduced pressure to obtain the title compound (166 mg). 1H-NMR (CDCl3) δ ppm: 3.94 (3H, s), 5.45 (2H, s), 5.51 (1H, br s), 6.61 (1H, d, J=0.4 Hz), 6.90-7.00 (2H, m). 7.15 (1H, dd, J=1.3, 5.0 Hz), 7.18 (1H, d, J=8.3 Hz), 7.24 (1H, dd, J=1.3, 2.9 Hz), 7.39 (1H, dd, J=2.9, 5.0 Hz), 7.65 (1H, br s), 7.75 (1H, t. J=7.8 Hz), 8.09 (1H, d, J=7.8 Hz).

Workup

  1. stirringby stirring for 66 more hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-697dc41a9f784255918f1570518625e9
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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