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Diisopropylethylamine → (+/-)-2-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]methyl]-N-[5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl]-4-oxazolecarboxamide

HRID 324410
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HRID 324410 반응식
[CH2:1]([C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[CH:8]([C:18]3[C:19](=[S:34])[NH:20][C:21](=[O:33])[N:22]([CH2:24][C:25]4[O:26][CH:27]=[C:28]([C:30]([OH:32])=O)[N:29]=4)[CH:23]=3)[C:6]=2[N:7]=1)[CH3:2].[NH2:35][C:36]1[N:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[NH:38][N:37]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:1]([C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[CH:8]([C:18]3[C:19](=[S:34])[NH:20][C:21](=[O:33])[N:22]([CH2:24][C:25]4[O:26][CH:27]=[C:28]([C:30]([NH:35][C:36]5[N:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[NH:38][N:37]=5)=[O:32])[N:29]=4)[CH:23]=3)[C:6]=2[N:7]=1)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 3508265-(trifluoromethyl)-4H-1,2,4-triazol-3-amineHCID 2733179PyBroPHCID 9826263(+/-)-2-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]methyl]-4-oxazolecarboxylic acid

생성물 1

HCID 86756617
(+/-)-2-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]methyl]-N-[5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl]-4-oxazolecarboxamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of the product of example 2 step (iii) (0.34 g), 4-(dimethylamino)pyridine (0.34 g), 3-amino-5-trifluoromethyl-1,2,4-triazole (J. Gen. Chem. USSR (Engl. Transl.) 1983, vol53, part 7, p1514) (0.42 g) and N,N-diisopropylethylamine (1.46 ml) in N,N-dimethylformamide (6 ml) was treated with bromo-tris(pyrrolidino)phosphonium hexafluorophosphate (1.3 g). After 2 hours the solution was quenched with aqueous tartaric acid. The solution was extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 30% ethyl acetate in toluene. The product was triturated with ethyl acetate/isohexane and the solid collected.

후처리

  1. customAfter 2 hours the solution was quenched with aqueous tartaric acid
  2. extractionThe solution was extracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with 30% ethyl acetate in toluene
  8. customThe product was triturated with ethyl acetate/isohexane
  9. customthe solid collected

출처 및 근거

ORD 기록
ord-ecd159ec57724d82b65ec4e0c69cef87
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06218376B1

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