1,2-Dichloroethane → 4-benzyloxy-N-[2,2-diethoxy-2-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-ethyl]-3-ethyl-5-methyl-benzamide

HRID 2069470노트

반응식

HRID 2069470 반응식
[CH2:1]([O:8][C:9]1[C:17]([CH3:18])=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.Cl.[NH2:46][CH2:47][C:48]([C:55]1[CH:60]=[C:59]([CH3:61])[N:58]=[C:57]([NH:62][CH:63]([CH3:65])[CH3:64])[N:56]=1)([O:52][CH2:53][CH3:54])[O:49][CH2:50][CH3:51]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9]1[C:17]([CH3:18])=[CH:16][C:12]([C:13]([NH:46][CH2:47][C:48]([O:52][CH2:53][CH3:54])([O:49][CH2:50][CH3:51])[C:55]2[CH:60]=[C:59]([CH3:61])[N:58]=[C:57]([NH:62][CH:63]([CH3:64])[CH3:65])[N:56]=2)=[O:15])=[CH:11][C:10]=1[CH2:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 594979194-Benzyloxy-3-ethyl-5-methyl-benzoic acidHCID 68505990[4-(2-Amino-1,1-diethoxy-ethyl)-6-methyl-pyrimidin-2-yl]-isopropyl-amine dihydrochloride

생성물 1

HCID 685084724-benzyloxy-N-[2,2-diethoxy-2-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-ethyl]-3-ethyl-5-methyl-benzamide수율 78.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-benzyloxy-3-ethyl-5-methyl-benzoic acid (224 mg, 0.83 mmol) in DMF (5 mL), EDC (175 mg, 0.91 mmol) and HOBt (124 mg, 0.91 mmol) are added. The mixture is stirred at rt for 15 min before DIPEA (0.57 mL, 3.3 mmol) and a solution of crude [4-(2-amino-1,1-diethoxy-ethyl)-6-methyl-pyrimidin-2-yl]-isopropyl-amine dihydrochloride (174 mg, 0.83 mmol) in DMF (2.0 mL) is added. The mixture is stirred at rt for 4 h, diluted with EtOAc (30 mL), and washed with sat. aq. NaHCO3 (15 mL) and brine (15 mL). The org. extract is dried over Na2SO4, filtered and concentrated. The crude product is purified on prep. TLC plates with Heptane/EtOAc 1:1 to give 4-benzyloxy-N-[2,2-diethoxy-2-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-ethyl]-3-ethyl-5-methyl-benzamide (348 mg) as a yellow oil; LC-MS: tR=1.02 min, [M+H]+=535.22.

후처리

  1. washwashed with sat. aq. NaHCO3 (15 mL) and brine (15 mL)
  2. extractionextract
  3. dry with materialis dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified on prep

출처 및 근거

ORD 기록
ord-0717560d4c1044bda090b7de2fec17fb
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299086B2

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