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Diisopropylethylamine → HCID 53246621, 화합물

HRID 1476524
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HRID 1476524 반응식
Cl.[CH3:2][S:3][CH2:4][C:5]1[N:9]=[C:8]([CH2:10][N:11]2[C:16]3[CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[S:19][C:15]=3[C:14](=[O:26])[N:13]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[C:12]2=[O:33])[O:7][N:6]=1.[CH2:34]([O:36][C:37]1[C:46]([O:47][CH3:48])=[CH:45][C:44]2[C:43]([C:49]3[CH:57]=[CH:56][C:52]([C:53](O)=[O:54])=[CH:51][CH:50]=3)=[N:42][C@@H:41]3[CH2:58][CH2:59][S:60][CH2:61][C@@H:40]3[C:39]=2[CH:38]=1)[CH3:35].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:34]([O:36][C:37]1[C:46]([O:47][CH3:48])=[CH:45][C:44]2[C:43]([C:49]3[CH:50]=[CH:51][C:52]([C:53]([N:30]4[CH2:31][CH2:32][CH:27]([N:13]5[C:14](=[O:26])[C:15]6[S:19][C:18]([C:20]7[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=7)=[CH:17][C:16]=6[N:11]([CH2:10][C:8]6[O:7][N:6]=[C:5]([CH2:4][S:3][CH3:2])[N:9]=6)[C:12]5=[O:33])[CH2:28][CH2:29]4)=[O:54])=[CH:56][CH:57]=3)=[N:42][C@@H:41]3[CH2:58][CH2:59][S:60][CH2:61][C@@H:40]3[C:39]=2[CH:38]=1)[CH3:35]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2회HCID 672584701-({3-[(methylsulfanyl)methyl]-1,2,4-oxadiazol-5-yl}methyl)-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride2회
HCID 67259092
4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid
2회

생성물 1

HCID 53246621HCID 53246621, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 1-({3-[(methylsulfanyl)methyl]-1,2,4-oxadiazol-5-yl}methyl)-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride (202.4 mg; compound B36), 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (159 mg; compound C10) and HBTU (167 mg) in DCM (8 ml) is added DIPEA (207 mg). The reaction mixture is stirred for 3 h at RT. Additional 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (80 mg; compound C10) and HBTU (84 mg) are added in order to complete the reaction. A saturated aqueous sodium bicarbonate solution (5 ml) is added and the mixture is extracted with DCM (25 ml). The phases are separated and the aqueous phase is extracted with further DCM (10 ml). The organic phases are combined and filtered using a phase separator. The organic layer is concentrated under reduced pressure and the residue is purified two times by flash column chromatography [amino phase silica gel, eluation gradient: cyclohexane/EtOAc, 100/0 to 0/100 (v/v)] to yield the title compound as a solid.

후처리

  1. customthe reaction
  2. extractionthe mixture is extracted with DCM (25 ml)
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with further DCM (10 ml)
  5. filtrationfiltered
  6. concentrationThe organic layer is concentrated under reduced pressure
  7. customthe residue is purified two times by flash column chromatography [amino phase silica gel, eluation gradient: cyclohexane/EtOAc, 100/0 to 0/100 (v/v)]

출처 및 근거

ORD 기록
ord-4d65897a34614df7a77568175a1eb97a
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018175B2

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