Ammonia → HCID 59456908, compound

HRID 1711899Notes

Reaction equation

HRID 1711899 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[N:3]1[C:8]1[N:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([N:18]([CH3:30])[CH2:19][C:20]2[N:21]([CH3:29])[C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:17])=[CH:10][CH:9]=1.[NH3:31]>>[CH3:30][N:18]([CH2:19][C:20]1[N:21]([CH3:29])[C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16](/[CH:15]=[CH:14]/[C:11]1[CH:10]=[CH:9][C:8]([NH:3][C:4](=[O:7])[CH2:5][CH2:6][C:2]([NH2:31])=[O:1])=[N:13][CH:12]=1)=[O:17]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 59456977HCID 59456977, compound

Product 1

HCID 59456908HCID 59456908, compoundYield 52%

Conditions

Temperature
60 °C

Procedure

A mixture of (E)-3-[6-(2,5-dioxo-pyrrolidin-1-yl)pyridin-3-yl]-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide (260 mg, 0.645 mmol) and ammonia (12 mL of 0.5M solution in 1,4-dioxane, 6.0 mmol) in a sealed tube was heated to 60° C. overnight. After cooling to ambient temperature, the resulting white precipitate was collected by filtration. The resulting solid was triturated with MeOH, washed with Et2O, and dried under high vacuum at 50° C. for 2 d to give the title compound (140 mg, 52%) as a white solid and as a mixture of amide rotamers: mp 225-227° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.67-10.63 (m, 1H), 8.62-8.58 (m, 1H), 8.21-8.07 (m, 2H), 7.60-7.25 (m, 5H), 7.12 (dd, J=7.7, 7.4 Hz, 1H), 7.00 (dd, J=7.3, 6.9 Hz, 1H), 6.77 (br s, 1H), 6.42-6.17 (m, 1H), 5.05-4.85 (m, 2H), 3.72-3.68 (m, 3H), 3.12-2.99 (m, 3H), 2.64-2.60 (m, 2H), 2.40-2.36 (m, 2H); MS (ESI) m/e 420 (M+H)+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe resulting white precipitate was collected by filtration
  3. customThe resulting solid was triturated with MeOH
  4. washwashed with Et2O
  5. customdried under high vacuum at 50° C. for 2 d

Sources & evidence

ORD record
ord-807f976a6830439690b875995140c32c
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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