Ammonia → HCID 57563006, compound

HRID 1726237Notes

Reaction equation

HRID 1726237 reaction equation
CO[C:3](=[O:44])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:34][C:35]2[CH:40]=[C:39]([C:41]#[N:42])[CH:38]=[CH:37][C:36]=2[F:43])[CH:13]2[CH2:18][CH2:17][N:16]([C@H:19]([CH3:33])[CH2:20][CH2:21][NH:22][C:23]([C:25]3[C:26]([CH3:32])=[N:27][CH:28]=[N:29][C:30]=3[CH3:31])=[O:24])[CH2:15][CH2:14]2)=[CH:8][CH:7]=1.[NH3:45]>CO>[C:3]([CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]([CH2:34][C:35]2[CH:40]=[C:39]([C:41]#[N:42])[CH:38]=[CH:37][C:36]=2[F:43])[CH:13]2[CH2:18][CH2:17][N:16]([C@H:19]([CH3:33])[CH2:20][CH2:21][NH:22][C:23]([C:25]3[C:30]([CH3:31])=[N:29][CH:28]=[N:27][C:26]=3[CH3:32])=[O:24])[CH2:15][CH2:14]2)=[CH:10][CH:11]=1)(=[O:44])[NH2:45]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57562978HCID 57562978, compound

Product 1

HCID 57563006HCID 57563006, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

COMPOUND 237 (74 mg, 0.12 mmol) was dissolved in MeOH (15 mL) and NH3(g) was passed through the solution for 10 minutes. The mixture was stirred at room temperature for 1 h then concentrated to give COMPOUND 239 as a yellow foam (72 mg, 100%). 1H NMR (CDCl3) δ 0.92-1.25 (m, 2H), 1.02 (d, 3H, J=6.6 Hz), 1.59 (m, 1H), 1.71-1.82 (m, 3H), 2.17 (m, 1H), 2.50 (s, 6H), 2.55 (m, 1H), 2.75-2.90 (m, 3H), 3.31-3.46 (m, 2H), 3.83 (m, 1H), 3.97 (s, 2H), 4.41 (s, 2H), 5.60 (br s, 1H), 6.60 (d, 2H, J=9.0 Hz), 6.76 (d, 2H, J=9.0 Hz), 7.17 (m, 1H), 7.52 (m, 2H), 8.23 (m, 1H), 8.84 (s, 1H). 13C NMR (CDCl3) δ 13.42, 21.92, 29.40, 30.42, 31.08, 39.81, 42.94, 43.79, 51.92, 58.25, 59.94, 67.83, 108.52, 115.69, 116.49, 116.80, 117.52, 118.34, 129.01, 129.21, 130.68, 132.73, 132.86, 133.32, 133.39, 142.87, 150.71, 157.58, 161.04, 162.97, 164.43, 166.40, 171.31. ES-MS m/z 588 (M+H). Anal. Calcd. for C32H38N7FO3.1.2CH4O: C, 63.69; H, 6.89; N, 15.66; F, 3.03. Found: C, 63.77; H, 6.68; N, 15.53; F, 2.87.

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-d39c2da7f18b4ce6b7c186011c1fa6d1
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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