Diisopropylethylamine → HCID 178490990, 화합물

HRID 2200909

반응식

HRID 2200909 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH2:5][NH:6][C:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]([N:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[CH2:21][OH:22])[N:8]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:61][C@H:62]1[CH2:67][CH2:66][C@H:65]([OH:68])[CH2:64][CH2:63]1>CN(C=O)C.O.C(OCC)(=O)C>[OH:68][C@H:65]1[CH2:66][CH2:67][C@H:62]([NH:61][C:13]([C:12]2[C:7]([NH:6][CH2:5][C:4]3[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:2]([Cl:1])[CH:3]=3)=[N:8][C:9]([N:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[CH2:21][OH:22])=[N:10][CH:11]=2)=[O:15])[CH2:63][CH2:64]1

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 671193354-[(3-Chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]pyrimidine-5-carboxylic acidHCID 178511715HCID 178511715, 화합물

생성물 1

HCID 178490990HCID 178490990, 화합물수율 31%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

In DMF (20 mL) was dissolved (s)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidine carboxylic acid (3.9 g, 10 mmol). The solution was cooled in an ice bath. HATU (5.67 g, 15 mmol) and DIPEA (1.93 g, 15 mmol) were added. After 20 min, trans-4-aminocyclohexanol (1.39 g, 12 mmol) was added in batches. The reaction was conducted overnight. LC-MS was used to monitor the reaction. Ethyl acetate (50 mL) and water (50 mL) were added. The separate aqueous phase was washed with ethyl acetate twice. The organic phase was combined, dried, concentrated and purified by silica gel column chromatography (VDCM:VMeOH=15:1) to give the product (1.5 g, 31% yield).

후처리

  1. temperatureThe solution was cooled in an ice bath
  2. waitThe reaction was conducted overnight
  3. customthe reaction
  4. washThe separate aqueous phase was washed with ethyl acetate twice
  5. customdried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (VDCM:VMeOH=15:1)

출처 및 근거

ORD 기록
ord-8e0f3bded7454bd69dfe3fd8298ea41a
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359371B2

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