Acetic Acid → HCID 178491008, compound

HRID 511641Notes

Reaction equation

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

Participants

Reactant 2

HCID 176Acetic Acid

HCID 67776470N-(2-amino-4-bromophenyl)-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)(methyl)amino)cyclobutyl)propanamide

Product 1

HCID 178491008HCID 178491008, compound

Procedure

A solution of N-(2-amino-4-bromophenyl)-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)(methyl)amino)cyclobutyl)propanamide (1.2 g, 1.6 mmol) in Acetic acid (4 ml, 70 mmol) was stirred overnight at 60° C., the volatiles were removed in vacuo and remaining residue purified directly by flash chromatography (DCM/7N NH3 in MeOH 91:9) to give (0.9 g) as a foam.

Workup

customthe volatiles were removed in vacuo
custompurified directly by flash chromatography (DCM/7N NH3 in MeOH 91:9)
customto give (0.9 g) as a foam

Sources & evidence

ORD record: ord-f3197827a22e4d3390cef50ecbbe3420
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096634B2

Reaction notes

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