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

HRID 253871노트

반응식

HRID 253871 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-270b6784532149d5b8f37103b28cc805
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872139B2

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