Cyanogen Bromide → Quinazolin-2-amine

HRID 41350

반응식

HRID 41350 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 FIG. 1, 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-16c12e29c27c4e31ace7baeccc73080c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530651B2

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