Dichloromethane → 1-Butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}indoline-6-carboxamide Hydrochloride

HRID 14161

반응식

HRID 14161 반응식
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=O)[CH:12]=2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:51][C@@H:52]([CH2:66][C:67]1[CH:72]=[C:71]([F:73])[CH:70]=[C:69]([F:74])[CH:68]=1)[C@H:53]([OH:65])[CH2:54][NH:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[C:59]([CH2:63][CH3:64])[CH:58]=1.C(Cl)[Cl:76]>C(N(CC)CC)C>[ClH:76].[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([NH:51][C@@H:52]([CH2:66][C:67]3[CH:68]=[C:69]([F:74])[CH:70]=[C:71]([F:73])[CH:72]=3)[C@H:53]([OH:65])[CH2:54][NH:55][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[C:59]([CH2:63][CH3:64])[CH:58]=3)=[O:16])[CH:12]=2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

참가 물질

7

반응물 5

HCID 6344DichloromethaneHCID 757711-HydroxybenzotriazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 210851761-Butylindoline-6-carboxylic acidHCID 57487282(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol

생성물 1

HCID 686080731-Butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}indoline-6-carboxamide Hydrochloride

시약·촉매·용매 1

HCID 8471Triethylamine용매

반응 조건

온도
40 °C

실험 절차

To a mixture of 1-butylindoline-6-carboxylic acid (0.2 g) in methylene chloride was added triethylamine (0.0.27 g), HOBT (0.125 g) and, HATU (0.347 g). The mixture was stirred at 40° C. for 15 minutes at which time (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (0.346 g) was added. The resulting mixture was stirred at 40° C. for 5 h then partitioned between water and methylene chloride. The layers were separated and the organic layer washed with water followed by brine and dried over anhydrous magnesium sulfate. Column chromatography on silica gel (100 mL) using 5% methanol in methylene chloride as eluent to give 0.100 g of the title compound: MS (ESI+) for C32H39F2N3O2 m/z 535.9 (M+H)+.

후처리

  1. additionwas added
  2. customthen partitioned between water and methylene chloride
  3. customThe layers were separated
  4. washthe organic layer washed with water
  5. dry with materialdried over anhydrous magnesium sulfate

출처 및 근거

ORD 기록
ord-ecb1e84a46ad4f18ad27f99bc3868de7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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