Trifluoroacetic acid → HCID 53250066, compound

HRID 2092800Notes

Reaction equation

HRID 2092800 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:14](=[O:15])[C:13]2[C:12]([NH:16][C:17]3[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=3)=[N:11][C:10]([CH2:24][CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)=[N:9][C:8]=2[CH2:7]1.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>>[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42].[NH2:27][CH2:26][CH2:25][CH2:24][C:10]1[N:11]=[C:12]([NH:16][C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)[C:13]2[C:14](=[O:15])[NH:6][CH2:7][C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58317712HCID 58317712, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 53250066HCID 53250066, compoundYield 65%

Conditions

Temperature
70 °C

Procedure

A mixture of tert-butyl 3-(6-(2,4-dimethoxybenzyl)-5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)propylcarbamate (1.7 mg, 0.003 mmol) in TFA (2 mL) was stirred at 70° C. for 2 h. The mixture was 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 (0.6 mg, 65%). 1H NMR (500 MHz, CD3OD) δ ppm 2.11-2.26 (m, 2H), 2.30-2.45 (m, 3H), 2.92-3.09 (m, 4H), 4.39 (s, 2H), 6.98 (d, J=8.34 Hz, 1H), 7.16-7.35 (m, 1H), 7.51 (s, 1H), 7.65 (d, J=8.59 Hz, 1H). [M+H] calc'd for C16H19N5O, 298. found, 298.

Workup

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

Sources & evidence

ORD record
ord-c0733e232fc14542b3ec56ce75780d7f
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

Loading…