HCID 67776851, compound → HCID 178491007, compound

HRID 511653Notes

Reaction equation

HRID 511653 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]([CH2:53][CH:54]2[CH2:56][CH2:55]2)[CH2:21][C@@H:22]2[C@@H:29]3[C@@H:25]([O:26][C:27]([CH3:31])([CH3:30])[O:28]3)[C@H:24]([N:32]3[C:36]4[N:37]=[CH:38][N:39]=[C:40]([NH:41][CH2:42][C:43]5[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][C:44]=5[O:51][CH3:52])[C:35]=4[CH:34]=[CH:33]3)[CH2:23]2)[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[CH2:17][CH:18]([N:20]([CH2:21][C@@H:22]4[C@H:29]5[O:28][C:27]([CH3:31])([CH3:30])[O:26][C@H:25]5[C@H:24]([N:32]5[C:36]6[N:37]=[CH:38][N:39]=[C:40]([NH:41][CH2:42][C:43]7[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][C:44]=7[O:51][CH3:52])[C:35]=6[CH:34]=[CH:33]5)[CH2:23]4)[CH2:53][CH:54]4[CH2:56][CH2:55]4)[CH2:19]3)=[N:1][C:2]=2[CH:7]=1)([CH3:10])([CH3:11])[CH3:9]

Participants

3

Reactant 1

HCID 67776851HCID 67776851, compound

Product 1

HCID 178491007HCID 178491007, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-(2-amino-4-(tert-butyl)phenyl)-3-(3-((cyclopropylmethyl)(((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)amino)cyclobutyl)propanamide (1.1 g, 1.4 mmol) in Acetic acid (5 ml) was heated at 60° C. overnight. The solution was concentrated and purified by flash chromatography (DCM/7N NH3 ion MeOH 93:7) to yield the desired compound (0.57 g) as a colorless foam.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by flash chromatography (DCM/7N NH3 ion MeOH 93:7)

Sources & evidence

ORD record
ord-fb71ed35c41846eea09904e33f685b69
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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