Ammonia → HCID 86707943, compound

HRID 2400291Notes

Reaction equation

[CH3:1][CH:2]([C:5]1[N:6]([CH2:17][C:18]2[N:23]=[C:22]([C:24](OC)=[O:25])[CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[C:9]([Cl:16])[CH:8]=2)[CH2:3][CH3:4].O1CCCC1.[NH3:33]>>[CH3:1][CH:2]([C:5]1[N:6]([CH2:17][C:18]2[N:23]=[C:22]([C:24]([NH2:33])=[O:25])[CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[C:9]([Cl:16])[CH:8]=2)[CH2:3][CH3:4]

Participants

Reactant 3

HCID 222Ammonia

HCID 8028Tetrahydrofuran

HCID 67685028HCID 67685028, compound

Product 1

HCID 86707943HCID 86707943, compound

Procedure

To a suspension of methyl 6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxylate (125 mg) in ammonia (Ca. 7 mol/L methanol solution, 20.1 mL) was added tetrahydrofuran (6.7 mL) at room temperature, followed by stirring for 27 hours. The reaction mixture was concentrated under reduced pressure to obtain the title compound (120 mg). 1H-NMR (CDCl3) δ ppm: 0.86 (3H, t, J=7.5 Hz), 1.25 (3H, d, J=6.9 Hz), 1.45-1.80 (2H, m), 2.65-2.80 (1H, m), 3.93 (3H, s), 5.39 (2H, s), 5.45-5.65 (1H, br), 6.30 (1H, s), 6.65-6.75 (1H, m), 7.11 (1H, s), 7.19 (1H, s), 7.60-7.80 (2H, m), 8.00-8.15 (1H, m).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-46853b343abc4a0d8cc3885139f8af24
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796247B2

Reaction notes

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