N-(2-amino-4-(trifluoromethoxy)phenyl)-3-(3-((((3 aR,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)(methyl)amino)cyclobutyl)propanamide → HCID 178491014, compound

HRID 511636Notes

Reaction equation

HRID 511636 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=O)[CH2:15][CH2:16][CH:17]1[CH2:20][CH:19]([N:21]([CH2:23][C@@H:24]2[C@@H:31]3[C@@H:27]([O:28][C:29]([CH3:33])([CH3:32])[O:30]3)[C@H:26]([N:34]3[C:38]4[N:39]=[CH:40][N:41]=[C:42]([NH:43][CH2:44][C:45]5[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][C:46]=5[O:53][CH3:54])[C:37]=4[CH:36]=[CH:35]3)[CH2:25]2)[CH3:22])[CH2:18]1>C(O)(=O)C>[CH3:54][O:53][C:46]1[CH:47]=[C:48]([O:51][CH3:52])[CH:49]=[CH:50][C:45]=1[CH2:44][NH:43][C:42]1[C:37]2[CH:36]=[CH:35][N:34]([C@H:26]3[C@H:27]4[C@H:31]([O:30][C:29]([CH3:33])([CH3:32])[O:28]4)[C@@H:24]([CH2:23][N:21]([CH3:22])[CH:19]4[CH2:18][CH:17]([CH2:16][CH2:15][C:14]5[NH:13][C:3]6[CH:4]=[CH:5][C:6]([O:8][C:9]([F:12])([F:10])[F:11])=[CH:7][C:2]=6[N:1]=5)[CH2:20]4)[CH2:25]3)[C:38]=2[N:39]=[CH:40][N:41]=1

Participants

3

Reactant 1

HCID 67776729N-(2-amino-4-(trifluoromethoxy)phenyl)-3-(3-((((3 aR,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)(methyl)amino)cyclobutyl)propanamide

Product 1

HCID 178491014HCID 178491014, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(2-amino-4-(trifluoromethoxy)phenyl)-3-(3-((((3 aR,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)(methyl)amino)cyclobutyl)propanamide (2 g, 2 mmol) in Acetic acid (4 ml) was stirred overnight at 60° C. The volatiles removed in vacuo and remaining residue purified by flash chromatography (DCM/7N NH3 in MeOH 92:8) to give the desired compound (1 g) as a solid.

Workup

  1. customThe volatiles removed in vacuo
  2. custompurified by flash chromatography (DCM/7N NH3 in MeOH 92:8)

Sources & evidence

ORD record
ord-776a8faba817425b867a6e7002cc435c
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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