Dimethylamine → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide

HRID 1945478Notes

Reaction equation

HRID 1945478 reaction equation
[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]4[O:18][C:19]5[CH:25]=[CH:24][C:23](C(O)=O)=[CH:22][C:20]=5[N:21]=4)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CNC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:67][N:68]([CH:70]=[O:71])[CH3:69]>>[CH3:67][N:68]([CH3:69])[C:70]([C:23]1[CH:24]=[CH:25][C:19]2[O:18][C:17]([CH2:16][O:15][C:14]3[CH:13]=[CH:12][C:11]([C:1]45[CH2:8][CH:7]6[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]6)[CH2:2]4)[CH2:10]5)=[CH:30][CH:29]=3)=[N:21][C:20]=2[CH:22]=1)=[O:71]

Participants

6

Reactant 5

HCID 674DimethylamineHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 249665342-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid

Product 1

HCID 249668972-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamideYield 59%

Procedure

To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (60.4 mg, 0.15 mmol), dimethyl amine (0.030 ml, in 2M THF) in DMF 5.0 mL was added HBTU (113.8 mg, 0.30 mmol) and DIPEA (0.052 ml, 0.30 mmol). After sting at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (n-Hexane:EtOAc:MeOH=15:3:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide as a white solid (37.9 mg, 59% yield).

Workup

  1. customAfter sting at room temperature
  2. customthe mixture was partitioned between ethyl acetate and brine
  3. dry with materialThe organic phase was dried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-Hexane:EtOAc:MeOH=15:3:1)

Sources & evidence

ORD record
ord-2a711e2948384c2096c68b7f37f4a7dc
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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