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

HRID 869127ノート

反応式

HRID 869127 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

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);

後処理

  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)

出典と根拠

ORDレコード
ord-591961557a044b8e81996aaf7472d4b3
出典データセット
uspto-grants-2015_03
特許番号
US08969360B2

反応ノート

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