Acetic Anhydride → HCID 57531383, compound

HRID 1091933Notes

Reaction equation

HRID 1091933 reaction equation
[NH2:1][CH2:2][C:3]1([OH:39])[CH2:8][CH2:7][N:6]([C:9]2[C:14]([CH2:15][N:16]([CH3:27])[C@@H:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19][CH2:18]3)=[C:13]([CH3:28])[N:12]=[C:11]([C:29]3[C:34]([CH2:35][CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=3[CH2:37][CH3:38])[N:10]=2)[CH2:5][CH2:4]1.C([O-])([O-])=O.[K+].[K+].[C:46](OC(=O)C)(=[O:48])[CH3:47].C([O-])(O)=O.[Na+]>CC(N(C)C)=O.CCOC(C)=O>[CH2:35]([C:34]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:37][CH3:38])[C:29]=1[C:11]1[N:10]=[C:9]([N:6]2[CH2:7][CH2:8][C:3]([CH2:2][NH:1][C:46](=[O:48])[CH3:47])([OH:39])[CH2:4][CH2:5]2)[C:14]([CH2:15][N:16]([CH3:27])[C@@H:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)=[C:13]([CH3:28])[N:12]=1)[CH3:36]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 57531498HCID 57531498, compound

Product 1

HCID 57531383HCID 57531383, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a vial containing 4-(aminomethyl)-1-[2-(2,6-diethylphenyl)-6-methyl-5-({methyl[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}methyl)pyrimidin-4-yl]piperidin-4-ol (25 mg, 0.047 mmol) in DMA (1.0 mL) is added K2CO3 (33 mg, 5.0 eq., 0.24 mmol) and acetic anhydride (0.023 mL, 5.0 eq., 0.24 mmol) and allowed to stir at room temperature for 16 h. EtOAc (2.0 mL) and sat NaHCO3 (2.0 mL) are then added and the organic layer is transferred directly onto a SiO2 plate and the product is eluted with 20:1 CHCl3:MeOH affording the title compound as a white foam. [mass expected (569.78); mass found (569.30)].

Workup

  1. additionare then added
  2. washthe product is eluted with 20:1 CHCl3

Sources & evidence

ORD record
ord-b5f6035ae735489aab29a67c3db5d540
Source dataset
uspto-grants-2012_03
Patent number
US08129395B2

Reaction notes

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