Butyryl chloride → tert-butyl [4-(4-amino-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate

HRID 1818139

반응식

HRID 1818139 반응식
[NH2:1]C1C=NC2C(C=1NCCCCNC(=O)OC(C)(C)C)=CC=C(Br)C=2.C(Cl)(=O)CCC.[Br:32][C:33]1[CH:34]=[CH:35][C:36]2[C:37]3[N:45]([CH2:46][CH2:47][CH2:48][CH2:49][NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])[C:44]([CH2:58][CH2:59][CH3:60])=[N:43][C:38]=3[CH:39]=[N:40][C:41]=2[CH:42]=1>>[NH2:1][C:39]1[C:38]2[N:43]=[C:44]([CH2:58][CH2:59][CH3:60])[N:45]([CH2:46][CH2:47][CH2:48][CH2:49][NH:50][C:51](=[O:57])[O:52][C:53]([CH3:54])([CH3:55])[CH3:56])[C:37]=2[C:36]2[CH:35]=[CH:34][C:33]([Br:32])=[CH:42][C:41]=2[N:40]=1

참가 물질

4

반응물 3

HCID 8855Butyryl chlorideHCID 21984174Tert-butyl [4-(3-amino-7-bromoquinolin-4-ylamino)butyl]carbamateHCID 86593760tert-butyl [4-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate

생성물 1

HCID 86593759tert-butyl [4-(4-amino-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate

실험 절차

tert-Butyl [4-(3-amino-7-bromoquinolin-4-ylamino)butyl]carbamate was treated with butyryl chloride and cyclized according to the methods described in Part C and D of Examples 125-135. The resulting product, tert-butyl [4-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate was oxidized and aminated according to the methods described in Parts H and I of Example 1 to afford tert-butyl [4-(4-amino-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate, which was coupled with 3-pyridylboronic acid according to the method described in Part J of Example 1. The reaction was heated at reflux for four hours, and the work-up procedure described in Part F of Examples 125-135 was followed. The crude product was recrystallized from toluene (1 mL/g) to provide tert-butyl {4-[4-amino-2-propyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate as a tan powder, mp 136-138° C.

출처 및 근거

ORD 기록
ord-cc3a95649c7a4425ba29fab10e5339e4
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598382B2

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