HCID 67776491, compound → HCID 178491012, compound

HRID 511613Notes

Reaction equation

HRID 511613 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F: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>[CH3:53][O:52][C:45]1[CH:46]=[C:47]([O:50][CH3:51])[CH:48]=[CH:49][C:44]=1[CH2:43][NH:42][C:41]1[C:36]2[CH:35]=[CH:34][N:33]([C@H:25]3[C@H:26]4[C@H:30]([O:29][C:28]([CH3:32])([CH3:31])[O:27]4)[C@@H:23]([CH2:22][N:20]([CH3:21])[CH:18]4[CH2:17][CH:16]([CH2:15][CH2:14][C:13]5[NH:12][C:3]6[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=6[N:1]=5)[CH2:19]4)[CH2:24]3)[C:37]=2[N:38]=[CH:39][N:40]=1

Participants

3

Reactant 1

HCID 67776491HCID 67776491, compound

Product 1

HCID 178491012HCID 178491012, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-(2-amino-4-(trifluoromethyl)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 (0.38 g, 0.50 mmol) and Acetic acid (5 ml) were stirred overnight at 65° C. The volatiles were removed in vacuo and remaining water was removed by azeotropic distillation with ethanol followed by 1 hour on high vacuum. The resulting residue was partitioned between NaHCO3 (saturated) and DCM. The aqueous layer was extracted (3×) and combined organics were dried with MgSO4, filtered, concentrated and then purified by flash chromatography (DCM/7N NH3 in MeOH 93:7) to yield an off white foam.

Workup

  1. customThe volatiles were removed in vacuo
  2. customwas removed by azeotropic distillation with ethanol
  3. customThe resulting residue was partitioned between NaHCO3 (saturated) and DCM
  4. extractionThe aqueous layer was extracted (3×)
  5. dry with materialcombined organics were dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography (DCM/7N NH3 in MeOH 93:7)
  9. customto yield an off white foam

Sources & evidence

ORD record
ord-f7aa42913dae4ab68c02f8412e267c19
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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