Cyanogen Bromide → Quinazolin-2-amine

HRID 2178727

반응식

HRID 2178727 반응식
[CH:1]1[C:6]2[N:7]=[C:8]3[N:13]([CH2:14][C:5]=2[C:4](Cl)=[C:3](Cl)[CH:2]=1)CC(=O)[NH:9]3.O.Cl.C(N(CC1C(N)=CC=C(Cl)C=1Cl)CC(O)=O)C.N#CBr>C1(C)C=CC=CC=1>[NH:9]=[C:8]1[N:13]=[CH:14][C:5]2[C:6](=[CH:1][CH:2]=[CH:3][CH:4]=2)[NH:7]1

참가 물질

6

반응물 4

HCID 10476Cyanogen Bromide2회HCID 21885828Hydrate;hydrochloride2회HCID 67080112ethyl-N-(6-amino-2,3-dichlorobenzyl)glycine2회HCID 135409400Anagrelide

생성물 1

HCID 178508286Quinazolin-2-amine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Commercially, as discussed in U.S. Pat. No. 5,801,245, and as shown in Scheme 1 below, anagrelide has been prepared as the hydrochloride monohydrate (compound IV) from the intermediate, ethyl-N-(6-amino-2,3-dichlorobenzyl)glycine (compound I), either by reaction with cyanogen bromide in hot alcoholic solution, or, preferentially, by reaction with cyanogen bromide in an aprotic solvent such as toluene to give the iminoquinazoline intermediate (compound II), which is isolated and then reacted with a base in a hot solution of alcohol to form anagrelide base (compound III).

출처 및 근거

ORD 기록
ord-1ab8ad0e7f384b0191570b857b431b25
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067944B2

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