Acetic Acid → HCID 178491011, compound

HRID 511615Notes

Reaction equation

HRID 511615 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]([CH2:22][C@@H:23]2[C@@H:30]3[C@@H:26]([O:27][C:28]([CH3:32])([CH3:31])[O:29]3)[C@H:25]([N:33]3[C:37]4[N:38]=[CH:39][N:40]=[C:41]([NH:42][CH2:43][C:44]5[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][C:45]=5[O:52][CH3:53])[C:36]=4[CH:35]=[CH:34]3)[CH2:24]2)[CH3:21])[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]([CH2:22][C@@H:23]4[C@H:30]5[O:29][C:28]([CH3:32])([CH3:31])[O:27][C@H:26]5[C@H:25]([N:33]5[C:37]6[N:38]=[CH:39][N:40]=[C:41]([NH:42][CH2:43][C:44]7[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][C:45]=7[O:52][CH3:53])[C:36]=6[CH:35]=[CH:34]5)[CH2:24]4)[CH3:21])[CH2:19]3)=[N:1][C:2]=2[CH:7]=1)([CH3:10])([CH3:9])[CH3:11]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 67774336N-(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)(methyl)amino)cyclobutyl)propanamide

Product 1

HCID 178491011HCID 178491011, compoundYield 86.6%

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)(methyl)amino)cyclobutyl)propanamide (0.24 g, 0.32 mmol) in Acetic acid (5 ml, 90 mmol) was stirred overnight at 60° C. The volatiles were removed in vacuo and remaining residue partitioned between Na2CO3 (2N) and DCM. The aqueous layer was extracted 3× with DCM and the combined organics dried with MgSO4, filtered and concentrated. The residue was purified by flash chromatography (DCM/7N NH3 in MeOH 94:6) to yield the desired compound (0.20 g) as a solid.

Workup

  1. customThe volatiles were removed in vacuo
  2. custompartitioned between Na2CO3 (2N) and DCM
  3. extractionThe aqueous layer was extracted 3× with DCM
  4. dry with materialthe combined organics dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (DCM/7N NH3 in MeOH 94:6)

Sources & evidence

ORD record
ord-2bc66d2be02147499a8a1cbe001dfe95
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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