1,2-Dichloroethane → 1-[4-(Pyrimidin-2-ylaminomethyl)-piperidin-1-yl]4-thiophen-2-yl-butan-1-one

HRID 1827213ノート

反応式

HRID 1827213 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17]CC2C=CC=CC=2)=O)[CH2:11][CH2:10]1.N1CCCCC1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[S:45]1[CH:49]=[CH:48][CH:47]=[C:46]1[CH2:50][CH2:51][CH2:52]C(O)=O>CN(C=O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[N:1][C:2]=1[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15](=[O:17])[CH2:52][CH2:51][CH2:50][C:46]2[S:45][CH:49]=[CH:48][CH:47]=2)[CH2:13][CH2:14]1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 783864-(2-Thienyl)Butyric AcidHCID 9923385Benzyl 4-[(2-pyrimidinylamino)methyl]-1-piperidinecarboxylate

生成物 1

HCID 221356711-[4-(Pyrimidin-2-ylaminomethyl)-piperidin-1-yl]4-thiophen-2-yl-butan-1-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Benzyl 4-[(2-pyrimidinylamino)methyl]-1-piperidinecarboxylate (EXAMPLE 16) was hydrogenated as described in EXAMPLE 30, Step 1. The resulting piperidine was combined with EDC (1.3 equiv.), HOBT (1.0 equiv.), and 4-thiophen-2-yl-butyric acid (1.0 equiv.) in DMF and stirred for 2 h. The resulting reaction solution was partitioned into ethyl acetate and aqueous sodium bicarbonate. The organic layer was seperated and washed with pH 4.5 citric acid buffer (10% citric acid and sodium hydroxide), dried (sodium sulfate), and concentrated to yield the desired 1-[4-(pyrimidin-2-ylaminomethyl)-piperidin-1-yl]-4-thiophen-2-yl-butan-1-one. M.S. (M+1): 345.25.

後処理

  1. customThe resulting reaction solution
  2. customwas partitioned into ethyl acetate and aqueous sodium bicarbonate
  3. customThe organic layer was seperated
  4. washwashed with pH 4.5 citric acid buffer (10% citric acid and sodium hydroxide)
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-8dcdaf91dbe64bf3bea6fcb554481fdb
出典データセット
uspto-grants-2006_05
特許番号
US07053089B2

反応ノート

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