Diisopropylethylamine → {4-[2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carbonyl]-piperazin-1-yl}-acetic acid ethyl ester

HRID 253871ノート

反応式

HRID 253871 の反応式
[CH:1]1([N:7]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8](=[O:18])[NH:9][C:10]2[S:11][C:12]([C:15]([OH:17])=O)=[CH:13][N:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1([C:31](=[O:39])[CH2:32][N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)CCOCC1.CN(C([O:47]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN([CH:70]([CH3:72])C)C(C)C>CCOC(C)=O.CN(C=O)C>[CH2:70]([O:47][C:31](=[O:39])[CH2:32][N:33]1[CH2:34][CH2:35][N:36]([C:15]([C:12]2[S:11][C:10]([NH:9][C:8]([N:7]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:18])=[N:14][CH:13]=2)=[O:17])[CH2:37][CH2:38]1)[CH3:72]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 1006221-(Morpholinocarbonylmethyl)piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114054472-(3,3-Dicyclohexylureido)thiazole-5-carboxylic acid

生成物 1

HCID 57883964{4-[2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carbonyl]-piperazin-1-yl}-acetic acid ethyl ester収率 49%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carboxylic acid (53 mg, 0.15 mmol), 1-morpholin-4-yl-2-piperazin-1-yl-ethanone (39 mg, 0.23 mmol), and HBTU (74 mg, 0.19 mmol) were weighed out and added to a 25 mL reaction flask. DMF (2 mL) and DIEA (52 μL, 0.30 mmol) were added. The reaction was stirred under nitrogen at ambient temperature overnight. The reaction was diluted with EtOAc (10 mL) and quenched with saturated aqueous NH4Cl (10 mL). After separation and extraction with EtOAc (2×5 mL) the combined organic portions were dried over MgSO4. Purification with silica gel chromatography (10% EtOAc and 1% MeOH in CH2Cl2) afforded 37 mg (49%) of the desired compound.

後処理

  1. additionadded to a 25 mL reaction flask
  2. customquenched with saturated aqueous NH4Cl (10 mL)
  3. customAfter separation and extraction with EtOAc (2×5 mL) the combined organic portions
  4. dry with materialwere dried over MgSO4
  5. customPurification with silica gel chromatography (10% EtOAc and 1% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-270b6784532149d5b8f37103b28cc805
出典データセット
uspto-grants-2011_01
特許番号
US07872139B2

反応ノート

読み込み中…