Trifluoroacetic acid → HCID 53252442, compound

HRID 711491Notes

Reaction equation

HRID 711491 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]([NH: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][NH: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 86654719HCID 86654719, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 53252442HCID 53252442, compoundYield 93%

Conditions

Temperature
70 °C

Procedure

A mixture of tert-butyl 2-(6-(2,4-dimethoxybenzyl)-5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamino)ethylcarbamate (0.055 g, 0.100 mmol) in TFA (2 mL) was stirred at 70° C. for 1.5 h. Following reaction, the solvent was removed and the resulting residue was dispersed into a solution of DMSO and MeOH (1/1). The mixture was filtered and the filtrate was purified by preparative HPLC. The fractions were collected and dried in vacuo to give a TFA salt of the title compound as an off-white solid (28 mg, 93%). 1H NMR (500 MHz, DMSO-d6) δ ppm 2.21-2.40 (m, 3H) 2.90-3.21 (m, 2H) 3.57 (q, J=5.86 Hz, 2H) 4.19 (br s, 2H) 6.90 (br s, 1H) 7.13-7.34 (m, 1H) 7.54 (br s, 1H) 7.56-7.74 (m, 2H) 7.80 (br s, 2H) 8.18 (d, J=13.67 Hz, 1H) 8.54-8.82 (m, 1H). [M+H] calc'd for C15H18N6O, 299. found, 299.

Workup

  1. customreaction
  2. customthe solvent was removed
  3. additionthe resulting residue was dispersed into a solution of DMSO and MeOH (1/1)
  4. filtrationThe mixture was filtered
  5. customthe filtrate was purified by preparative HPLC
  6. customThe fractions were collected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-027a4d73683c4d60ad440091a4b3a46c
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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