Triethylamine → tert-butylN-[1-[[4-chloro-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

HRID 535427ノート

反応式

HRID 535427 の反応式
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])[CH3:3].[Cl:14][C:15]1[CH:20]=[C:19]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=[C:17]([NH2:29])[CH:16]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CN1C(=O)CCC1>[C:2]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH3:13])[C:10]([NH:29][C:17]1[CH:16]=[C:15]([Cl:14])[CH:20]=[C:19]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1)=[O:12])([CH3:1])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 2684712-N-Boc-aminopropionic acid2 回HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866943684-Chloro-6-(2-phenylethynyl)pyridin-2-amine

生成物 1

HCID 86694418tert-butylN-[1-[[4-chloro-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
40 °C

実験手順

A mixture of 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid (1.17 g, 6.19 mmol), 4-chloro-6-(2-phenylethynyl)pyridin-2-amine B3a (1.09 g, 4.76 mmol), triethylamine (3.63 ml, 25.7 mmol) HATU (2.89 g, 7.61 mmol) and NMP (3.75 ml) is stirred at 40° C. for 60 h. 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid (0.72 g, 3.81 mmol) and HATU (1.45 g, 3.81 mmol) is added to the mixture and stirring continued for 48 h at 60° C. At RT water is added and the mixture extracted with DCM. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 712 mg (37%). HPLC-MS: M+H=400; tR=2.27 min (*Method—2).

後処理

  1. stirringstirring
  2. waitcontinued for 48 h at 60° C
  3. extractionthe mixture extracted with DCM
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product is purified by RP HPLC

出典と根拠

ORDレコード
ord-df391ad61e0547c8affff740ed09ea1e
出典データセット
uspto-grants-2014_10
特許番号
US08859541B2

反応ノート

読み込み中…