Diisopropylethylamine → HCID 67777045, compound

HRID 511659Notes

Reaction equation

HRID 511659 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:4]=1[CH2:5][NH:6][C:7]1[N:15]=[CH:14][N:13]=[C:12]2[C:8]=1[N:9]=[CH:10][N:11]2[C@H:16]1[C@@H:20]2[O:21]C(C)(C)[O:23][C@@H:19]2[C@@H:18]([CH2:26][N:27]([CH:37]([CH3:39])[CH3:38])[CH:28]2[CH2:31][CH:30]([CH2:32][CH2:33][C:34]([OH:36])=O)[CH2:29]2)[CH2:17]1.C(N(CC)C(C)C)(C)C.[C:55]([C:59]1[CH:60]=[C:61]([NH2:66])[C:62]([NH2:65])=[CH:63][CH:64]=1)([CH3:58])([CH3:57])[CH3:56].C([O-])(O)=O.[Na+]>CN(C)C=O>[NH2:66][C:61]1[CH:60]=[C:59]([C:55]([CH3:57])([CH3:56])[CH3:58])[CH:64]=[CH:63][C:62]=1[NH:65][C:34](=[O:36])[CH2:33][CH2:32][CH:30]1[CH2:31][CH:28]([N:27]([CH2:26][C@H:18]2[CH2:17][C@@H:16]([N:11]3[CH:10]=[N:9][C:8]4[C:12]3=[N:13][CH:14]=[N:15][C:7]=4[NH:6][CH2:5][C:4]3[CH:40]=[CH:41][C:42]([O:44][CH3:45])=[CH:43][C:3]=3[O:2][CH3:1])[C@H:20]([OH:21])[C@@H:19]2[OH:23])[CH:37]([CH3:38])[CH3:39])[CH2:29]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4327084-Tert-butylbenzene-1,2-diamineHCID 516892Sodium BicarbonateHCID 67777212HCID 67777212, compound

Product 1

HCID 67777045HCID 67777045, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N,N′,N′-Tetramethyl-0-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (1.19 g, 3.13 mmol) added to a solution of 3-{3-[{[(3aR,4R,6R,6aS)-6-{6-[(2,4-dimethoxybenzyl)amino]-9H-purin-9-yl}-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl}{isopropyl)amino]cyclobutyl}propanoic acid (1.30 g, 2.09 mmol) and N,N-Diisopropylethylamine (1.20 ml, 6.89 mmol) and 4-tert-butylbenzene-1,2-diamine (0.411 g, 2.50 mmol) in N,N-Dimethylformamide (12.9 ml). The reaction was stirred for 2 hours, NaHCO3 (saturated) was added and the mixture extracted with EtOAc (3×) and the combined organics was dried over MgSO4 filtered and concentrated. The residue was purified by flash chromatography (DCM→DCM/7N NH3 in MeOH 95:5) to yield the desired amide (1.4 g) as a solid.

Workup

  1. extractionthe mixture extracted with EtOAc (3×)
  2. dry with materialthe combined organics was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (DCM→DCM/7N NH3 in MeOH 95:5)

Sources & evidence

ORD record
ord-0560d7b3b3cd4e1e90694312d241ef68
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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