Trifluoroacetic acid → Trifluoroacetic acid

HRID 516032Notes

Reaction equation

HRID 516032 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:14](=[O:15])[C:13]2[C:12]([C:16]3[CH:17]=[N:18][N:19]([CH3:22])[C:20]=3[CH3:21])=[N:11][C:10]([NH:23][C@@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]3[NH:30]C(=O)OC(C)(C)C)=[N:9][C:8]=2[CH2:7]1.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>>[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45].[NH2:30][C@H:25]1[CH2:26][CH2:27][CH2:28][CH2:29][C@H:24]1[NH:23][C:10]1[N:11]=[C:12]([C:16]2[CH:17]=[N:18][N:19]([CH3:22])[C:20]=2[CH3:21])[C:13]2[C:14](=[O:15])[NH:6][CH2:7][C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86696605HCID 86696605, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 58317686HCID 58317686, compound

Conditions

Temperature
70 °C

Procedure

A mixture of tert-butyl (1S,2R)-2-(6-(2,4-dimethoxybenzyl)-4-(1,5-dimethyl-1H-pyrazol-4-yl)-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamino)cyclohexylcarbamate obtained above in TFA (2 mL) was stirred at 70° C. for 2 h. The mixture was subsequently purified by reverse phase preparative HPLC. The fractions were collected and concentrated to give a TFA salt of the title compound as a white solid (0.5 mg). 1H NMR (500 MHz, CD3OD) δ ppm 1.59 (br s, 2 H), 1.67-2.02 (m, 6 H), 2.66-2.72 (m, 3 H), 3.67 (br s, 1 H), 3.85 (s, 3 H), 4.29 (s, 2 H), 4.50-4.64 (m, 1 H), 8.64 (br s, 1 H). [M+H] calc'd for C17H23N7O, 342; found, 342.

Workup

  1. customThe mixture was subsequently purified by reverse phase preparative HPLC
  2. customThe fractions were collected
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d76d25bce51f4dccbc91366410b2cd55
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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