Trifluoroacetic acid → 3-Amino-4-chloro-5-(2-(morpholine-4-carbonyl)morpholino)benzonitrile

HRID 921671노트

반응식

HRID 921671 반응식
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[O:15])[CH2:9]2)=[CH:6][C:5]([C:22]#[N:23])=[CH:4][C:3]=1[NH:24]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:24][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[O:15])[CH2:9]2)[C:2]=1[Cl:1])[C:22]#[N:23]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86708537Tert-butyl (2-chloro-5-cyano-3-(2-(morpholine-4-carbonyl)morpholino)phenyl)carbamate

생성물 1

HCID 867085363-Amino-4-chloro-5-(2-(morpholine-4-carbonyl)morpholino)benzonitrile수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a round bottom flask charged with tert-butyl (2-chloro-5-cyano-3-(2-(morpholine-4-carbonyl)morpholino)phenyl)carbamate (91 mg, 0.202 mmol) was added dichloromethane (1076 μl) and TFA (269 μl). The reaction mixture was stirred at room temperature 3 h. Excess TFA was removed by concentration in vacuo. The crude residue was free based using a Phenomenex Strata 1 g SCX column. The column was flushed with 3 column volumes methanol and 3 column volumes 3.5 N ammonia/methanol. The ammonia layers were concentrated in vacuo to provide 3-amino-4-chloro-5-(2-(morpholine-4-carbonyl)morpholino)benzonitrile (68 mg, 0.194 mmol, 96%)

후처리

  1. customExcess TFA was removed by concentration in vacuo
  2. customThe column was flushed with 3 column volumes methanol and 3 column volumes 3.5 N ammonia/methanol
  3. concentrationThe ammonia layers were concentrated in vacuo

출처 및 근거

ORD 기록
ord-212391f1a7f041d29cdbe5f1255805e5
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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