Ammonia → Rilpivirine

HRID 2280429노트

반응식

HRID 2280429 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12](/[CH:16]=[CH:17]/[C:18]#[N:19])=[CH:11][C:10]=2[CH3:20])[CH:5]=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N>C(O)(C)C>[CH3:20][C:10]1[CH:11]=[C:12](/[CH:16]=[CH:17]/[C:18]#[N:19])[CH:13]=[C:14]([CH3:15])[C:9]=1[NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=2)[N:7]=1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 6101p-Toluenesulfonic acidHCID 133964-AminobenzonitrileHCID 72721606HCID 72721606, 화합물

생성물 1

HCID 6451164Rilpivirine수율 77.7%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
82.5 °C

실험 절차

To a mixture of (E)-3-(4-(2-chloropyrimidin-4-ylamino)-3,5-dimethylphenyl)acrylonitrile (40 gm), 4-aminobenzonitrile (17 gm), isopropanol (400 ml) and p-toluenesulfonic acid (20 ml) were added at room temperature. The reaction mixture was then heated to 80 to 85° C. and stirred for 4 hours. The reaction mass was then cooled to 0° C. and pH was adjusted to 10 to 11 with aqueous ammonia solution. The separated solid was filtered and then dried to provide 40 gm of rilpivirine.

후처리

  1. additionwere added at room temperature
  2. temperatureThe reaction mass was then cooled to 0° C.
  3. filtrationThe separated solid was filtered
  4. customdried

출처 및 근거

ORD 기록
ord-2ae6918ee7b041b9abef86dac4a38581
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139535B2

반응 노트

불러오는 중…