N-(2-amino-4-(tert-butyl)phenyl)-3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isobutyl)amino)cyclobutyl)propanamide → HCID 178491018, compound

HRID 2040697Notes

Reaction equation

HRID 2040697 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[CH2:14][CH2:15][CH:16]1[CH2:19][CH:18]([N:20]([CH2:25][C@@H:26]2[C@@H:33]3[C@@H:29]([O:30][C:31]([CH3:35])([CH3:34])[O:32]3)[C@H:28]([N:36]3[C:40]4[N:41]=[CH:42][N:43]=[C:44]([NH:45][CH2:46][C:47]5[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][C:48]=5[O:55][CH3:56])[C:39]=4[CH:38]=[CH:37]3)[CH2:27]2)[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:17]1>C(O)(=O)C>[C:8]([C:6]1[CH:5]=[CH:4][C:3]2[NH:12][C:13]([CH2:14][CH2:15][CH:16]3[CH2:19][CH:18]([N:20]([CH2:25][C@@H:26]4[C@H:33]5[O:32][C:31]([CH3:34])([CH3:35])[O:30][C@H:29]5[C@H:28]([N:36]5[C:40]6[N:41]=[CH:42][N:43]=[C:44]([NH:45][CH2:46][C:47]7[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][C:48]=7[O:55][CH3:56])[C:39]=6[CH:38]=[CH:37]5)[CH2:27]4)[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:17]3)=[N:1][C:2]=2[CH:7]=1)([CH3:9])([CH3:11])[CH3:10]

Participants

3

Reactant 1

HCID 67774095N-(2-amino-4-(tert-butyl)phenyl)-3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isobutyl)amino)cyclobutyl)propanamide

Product 1

HCID 178491018HCID 178491018, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(2-amino-4-(tert-butyl)phenyl)-3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isobutyl)amino)cyclobutyl)propanamide (1.71 g, 2.19 mmol) in Acetic acid (6 ml) was stirred overnight at 60° C., the volatiles were removed in vacuo and the remaining residue was purified by flash chromatography (SiO2, DCM/7N NH3 in MeOH 94:6) to yield the desired compound (0.9 g) as a foam,

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe remaining residue was purified by flash chromatography (SiO2, DCM/7N NH3 in MeOH 94:6)

Sources & evidence

ORD record
ord-d766554d38dd4294a95f58cd5d36f05a
Source dataset
uspto-grants-2013_11
Patent number
US08580762B2

Reaction notes

Loading…