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

HRID 1945479노트

반응식

HRID 1945479 반응식
[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:26]([OH:28])=O)=CC=5N=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.C([NH2:37])C1OC=CC=1.[CH2:38](Cl)[CH2:39]Cl.C1C=CC2N(O)N=NC=2C=1.C[CH2:53][N:54]([CH:58](C)C)C(C)C>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[CH3:53][N:54]([CH3:58])[C:26]([C:23]1[CH:24]=[CH:25][C:19]2[O:18][C:17]([CH2:16][O:15][C:14]3[CH:29]=[CH:30][C:11]([C:1]45[CH2:8][CH:7]6[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]6)[CH2:10]4)[CH2:2]5)=[CH:12][CH:13]=3)=[N:37][C:38]=2[CH:39]=1)=[O:28]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 3438FurfurylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 249665342-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid

생성물 1

HCID 249668972-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide수율 95.5%

시약·촉매·용매 1

HCID 70262,4,6-Tris((dimethylamino)methyl)phenol용매

실험 절차

To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (30.1 mg, 0.08 mmol), furfuryl amine (11.0 mg, 0.12 mmol, 0.01 ml), EDC (21.7 mg, 0.12 mmol) and HOBt (15.4 mg, 0.12 mmol) in DMF 3.0 mL was added DIPEA (14.2 mg, 0.12 mmol, 0.02 ml). After string 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=6:3:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide as a white solid (32.9 mg, 90.9% yield).

후처리

  1. customAfter string at room temperature, the mixture was partitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (n-Hexane:EtOAc:MeOH=6:3:1)

출처 및 근거

ORD 기록
ord-7ab7cd6ccbd24ca99f72be340fac1f4f
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394799B2

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