Trifluoroacetic acid → Trifluoroacetic acid

HRID 2092886Notes

Reaction equation

HRID 2092886 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=2)[C:12]2[C:21](=[O:36])[N:22](CC3C=CC(OC)=CC=3OC)[CH:23]([CH3:24])[C:11]=2[C:10]=1[F:37].[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=2)[C:12]2[C:21](=[O:36])[NH:22][CH:23]([CH3:24])[C:11]=2[C:10]=1[F:37].[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67238382HCID 67238382, compound

Product 2

HCID 6422Trifluoroacetic acidYield 71%HCID 53251011HCID 53251011, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 6-((1R,2S)-2-aminocyclohexylamino)-2-(2,4-dimethoxybenzyl)-7-fluoro-1-methyl-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one (20 mg, 0.039 mmol) and TFA (1 mL) was heated at 60° C. for 2 h. Following reaction, the mixture was purified by preparative HPLC eluting with water (0.05% TFA) and ACN (15-25% gradient, 0.035% TFA) to give the title compound as a TFA salt (10 mg, 71%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.41 (d, J=6.59 Hz, 3H), 1.46 (d, J=7.02 Hz, 2H), 1.60-1.84 (m, 5H), 3.68 (br s, 1H), 3.89 (s, 2H), 4.44 (br s, 1H), 4.71 (q, J=6.65 Hz, 1H), 6.52 (br s, 1H), 6.73 (d, J=6.53 Hz, 1H), 7.72 (br s, 2H), 8.24-8.32 (m, 1H), 8.46 (s, 1H), 8.82 (s, 1H). [M+H] calc'd for C18H23FN6O, 359. found, 359.

Workup

  1. customreaction
  2. customthe mixture was purified by preparative HPLC
  3. washeluting with water (0.05% TFA) and ACN (15-25% gradient, 0.035% TFA)

Sources & evidence

ORD record
ord-3b9017c748d04af69167ec1048d20ecb
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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