Hydrochloric Acid → HCID 90039531, compound

HRID 526019Notes

Reaction equation

HRID 526019 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[CH:12]=[C:11]([C:13]([NH:15][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:17]([F:20])([F:19])[F:18])=[O:14])[N:10]([CH2:31][CH3:32])[C:6]2=[N:7][C:8]=1[CH3:9].[C:33](Cl)(=[O:35])[CH3:34].Cl>N1C=CC=CC=1>[C:33]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]2[CH:12]=[C:11]([C:13]([NH:15][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:17]([F:18])([F:19])[F:20])=[O:14])[N:10]([CH2:31][CH3:32])[C:6]2=[N:7][C:8]=1[CH3:9])(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 118275227HCID 118275227, compound

Product 1

HCID 90039531HCID 90039531, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-(Aminomethyl)-1-ethyl-6-methyl-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (70.0 mg, 0.15 mmol) was initially charged in pyridine (1.7 ml), acetyl chloride (14.4 mg, 0.18 mmol) was added and the mixture was stirred at room temperature for 2 hours. Ice-water was added, the reaction mixture was acidified with 2N HCl and the precipitated product was filtered off. After drying, the product was chromatographed using cyclohexane/ethyl acetate (1/1), which gave 5.00 mg (6.5% of theory) of 5-(acetamidomethyl)-1-ethyl-6-methyl-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-pyrrolo[2,3-b]pyridine-2-carboxamide. HPLC-MS: log P=3.16; mass (m/z): 501.1 (M+H)+; 1HNMR (D6-DMSO): δ 1.23 (t, 2H), 2.57 (s, 3H), 3.32 (s, 3H), 4.34 (m, 2H), 4.58 (q, 2H), 6.28-6.30 (m, 1H), 7.30 (s, 1H), 7.70-7.87 (m, 2H), 8.05 (d, 1H), 8.20 (s, 1H), 8.25 (m, 1H), 9.68 (m, 1H).

Workup

  1. filtrationthe precipitated product was filtered off
  2. customAfter drying
  3. customthe product was chromatographed

Sources & evidence

ORD record
ord-470ffc10aecc4c0687cbf37461b0001e
Source dataset
uspto-grants-2016_05
Patent number
US09345247B2

Reaction notes

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