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

HRID 2069470ノート

反応式

HRID 2069470 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0717560d4c1044bda090b7de2fec17fb
出典データセット
uspto-grants-2012_10
特許番号
US08299086B2

反応ノート

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