Triethylamine → 2-amino-5-(2-(dimethylamino)ethoxy)-N-(4-methylpyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 869127노트

반응식

HRID 869127 반응식
[NH2:1][C:2]1[C:16]([C:17]([OH:19])=O)=[C:5]2[N:6]=[C:7]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[CH:8]=[CH:9][N:4]2[N:3]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:49][C:50]1[CH:55]=[CH:54][N:53]=[CH:52][C:51]=1[NH2:56]>CN1C(=O)CCC1>[NH2:1][C:2]1[C:16]([C:17]([NH:56][C:51]2[CH:52]=[N:53][CH:54]=[CH:55][C:50]=2[CH3:49])=[O:19])=[C:5]2[N:6]=[C:7]([O:10][CH2:11][CH2:12][N:13]([CH3:14])[CH3:15])[CH:8]=[CH:9][N:4]2[N:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 1379353-Amino-4-picolineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 904115212-Amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

생성물 1

HCID 904186462-amino-5-(2-(dimethylamino)ethoxy)-N-(4-methylpyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide수율 42%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
100 °C

실험 절차

To a suspension of 2-amino-5-[2-(dimethylamino)ethoxy]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (100 mg, 0.377 mmol) in NMP (667 μL) was added Et3N (46.54 mg, 64.1 μL, 0.4599 mmol) in one portion. The mixture was stirred for 10 minutes before adding TBTU (Boron Tetrafluoride Ion) (136.3 mg, 0.4245 mmol), portionwise, over 5 minutes. The mixture was allowed to stir at room temperature for 20 mins. 4-Methylpyridin-3-amine (40.77 mg, 0.377 mmol) was added and the mixture was heated to 100° C. for 4 hours. The mixture was filtered through a silica gel pad and eluted with DCM initially followed by 20/80 MeOH/DCM. The residue was further purified by preparative HPLC to provide compound I-C-3 (42% yield). LC-MS (M+H)+=356.2; 1H NMR (500 MHz, DMSO-d6) δ 9.80 (s, 1H), 9.38 (brs, 1H), 9.20 (brs, 1H), 8.82 (d, 1H), 8.50-8.43 (m, 1H), 7.66-7.6 (m, 1H), 6.62 (d, 1H), 6.50 (brs, 2H), 4.81-4.78 (m, 2H), 3.63-3.60 (m, 2H), 2.95 (s, 6H), 2.55 (s, 3H);

후처리

  1. waitportionwise, over 5 minutes
  2. stirringto stir at room temperature for 20 mins
  3. filtrationThe mixture was filtered through a silica gel pad
  4. washeluted with DCM
  5. customThe residue was further purified by preparative HPLC
  6. customto provide compound I-C-3 (42% yield)

출처 및 근거

ORD 기록
ord-591961557a044b8e81996aaf7472d4b3
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969360B2

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