HCID 178427769, compound → HCID 178421987, compound

HRID 2053017Notes

Reaction equation

HRID 2053017 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:12]=3)=[C:9]([CH3:25])[N:8]([C@H:26]3[CH2:29][C@H:28]([CH2:30]OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:27]3)[C:4]=2[N:5]=[CH:6][N:7]=1>N1CCCC1>[CH2:18]([O:17][C:13]1[CH:12]=[C:11]([C:10]2[C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([C@H:26]3[CH2:27][C@H:28]([CH2:30][N:8]4[CH2:9][CH2:10][CH2:3][CH2:4]4)[CH2:29]3)[C:9]=2[CH3:25])[CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 178427769HCID 178427769, compound

Product 1

HCID 178421987HCID 178421987, compound

Reagents, catalysts & solvents 1

HCID 31268PyrrolidineSolvent

Procedure

0.335 g (0.589 mmol) trans-toluene-4-sulfonic acid 3-[4-amino-5-(3-benzyloxy-phenyl)-6-methyl-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl ester of Example 106 in 3.6 ml pyrrolidine are stirred at RT for 3.5 h (Thin Layer Chromatography and HPLC control). The excess reagent is evaporated on a rotavap and the residue purified by chromatography (solvent: ethyl acetate-MeOH-aqu. NH3 (33%) 95:5:1). The compound is crystallized from diethylether. Analytical HPLC: tR=9.09 min (Grad 1); mp: 136-140° C.; ES-MS: m/eo=468.3; NMR (DMSO-d6; not all signals reported): 8.10/s (1H), 7.25-7.5/several m's (6H), 7.02/“d” (1H); 6.94/s (1H); 6.89/“d” (1H); 5.5-6.0/b (NH2); 5.13/s (2H); 5.06/m (1H); 2.22/s (3H).

Workup

  1. customThe excess reagent is evaporated on a rotavap
  2. customthe residue purified by chromatography (solvent: ethyl acetate-MeOH-aqu. NH3 (33%) 95:5:1)
  3. customThe compound is crystallized from diethylether

Sources & evidence

ORD record
ord-7d1489a0400b4514b53b10c50c5b9fb0
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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