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

HRID 1945478ノート

反応式

HRID 1945478 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2a711e2948384c2096c68b7f37f4a7dc
出典データセット
uspto-grants-2013_03
特許番号
US08394799B2

反応ノート

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