Ethylamine → HCID 178465182、化合物

HRID 571415ノート

反応式

HRID 571415 の反応式
[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]

参加物

8

反応物 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

生成物 1

HCID 178465182HCID 178465182、化合物収率 53.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-f130e765b1414437ae14a2d002676307
出典データセット
uspto-grants-2015_05
特許番号
US09023865B2

反応ノート

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