Diisopropylethylamine → HCID 178455274, 화합물

HRID 2169321노트

반응식

HRID 2169321 반응식
[CH2:1]([O:8][C:9]1[C:10]([C:28]([OH:30])=O)=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:31]([O:38][CH2:39][CH2:40][NH:41][CH:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[Si:31]([O:38][CH2:39][CH2:40][N:41]([CH:42]1[CH2:43][CH2:44][CH2:45][CH2:46]1)[C:28]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:14]([OH:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]=1)=[O:30])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

참가 물질

7

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 86725959[2-(Tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopentylamineHCID 178524866HCID 178524866, 화합물

생성물 1

HCID 178455274HCID 178455274, 화합물수율 62.28%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution mixture of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (283) (100 mg, 0.25 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopentyl-amine (8e) (72 mg, 0.29 mmol) in dimethylformamide (2.5 mL) were added N,N-diisopropylethylamine (0.1 mL, 0.74 mmol) and HATU (141 mg, 0.37 mmol). Stirring was continued at room temperature for 20 h, whereafter water (25 mL) was added and the mixture extracted with ethyl acetate (3×20 mL). The combined organic part was washed with water (3×50 mL) and brine (2×30 mL) and dried and concentrated. The crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopentyl-amide (288) (97 mg, 62.28%) as a light yellow sticky solid.

후처리

  1. additionwas added
  2. extractionthe mixture extracted with ethyl acetate (3×20 mL)
  3. washThe combined organic part was washed with water (3×50 mL) and brine (2×30 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-97eded13c0e24a8184a8e1f18f11e70f
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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