Ethylamine → HCID 178465182, 화합물

HRID 571415노트

반응식

HRID 571415 반응식
[CH3:1][O:2][CH2:3][C@@H:4]([NH:11][C:12](=[O:48])[NH:13][C:14]1[N:19]=[CH:18][C:17]2[C:20]([C@@H:42]3[CH2:44][C@H:43]3[C:45](O)=[O:46])=[N:21][N:22](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:16]=2[CH:15]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[CH3:67][CH2:68][N:69](C(C)C)C(C)C.C(N)C.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH2:68]([NH:69][C:45]([C@@H:43]1[CH2:44][C@H:42]1[C:20]1[C:17]2[CH:18]=[N:19][C:14]([NH:13][C:12]([NH:11][C@@H:4]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:3][O:2][CH3:1])=[O:48])=[CH:15][C:16]=2[NH:22][N:21]=1)=[O:46])[CH3:67]

참가 물질

8

반응물 6

HCID 6341EthylamineHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 89525877trans-2-(6-(3-((S)-2-methoxy-1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxylic acid

생성물 1

HCID 178465182HCID 178465182, 화합물수율 53.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of trans-2-(6-(3-((S)-2-methoxy-1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxylic acid (13 mg, 0.020 mmol), 1-propanephosphonic acid cyclic anhydride (50% in EtOAc, 18.20 μl, 0.031 mmol), DIEA (10.68 μl, 0.061 mmol) and ethylamine (2M in THF) (102 μl, 0.204 mmol) in DCM (0.5 ml) was stirred at room temperature overnight and then concentrated. The residue was treated with TFA (500 μl, 6.49 mmol) and triethylsilane (7 μl, 0.044 mmol). The mixture was stirred at room temperature for 6 h and then concentrated. The residue was purified by preparative HPLC (Reverse phase C-18, Waters SunFire PrepODB, 150×19 mm, 5u), eluting with 10-90% Acetonitrile/Water+0.1% TFA (20 mL/min) over 15 min. to give trans-N-ethyl-2-(6-(3-((S)-2-methoxy-1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxamide (4.5 mg, 52% yield). MS ESI calc'd. for C22H26N6O3[M+1]+ 423, found 423. MS ESI calc'd. for C22H26N6O3[M−1]− 421, found 421.

후처리

  1. concentrationconcentrated
  2. stirringThe mixture was stirred at room temperature for 6 h
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC (Reverse phase C-18, Waters SunFire PrepODB, 150×19 mm, 5u)
  5. washeluting with 10-90% Acetonitrile/Water+0.1% TFA (20 mL/min) over 15 min.

출처 및 근거

ORD 기록
ord-f130e765b1414437ae14a2d002676307
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023865B2

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