Triethylamine → HCID 178522415、化合物

HRID 2064623ノート

反応式

HRID 2064623 の反応式
FC(F)[O:3][C:4]1[CH:26]=[CH:25][C:7]2NC(C3C(NC(N4CCCCC4)=O)=CNN=3)=NC=2C=1.[NH:28]1[C:39]2[C:31](=[CH:32][C:33]3[CH2:34][CH2:35][CH2:36][C:37]=3[CH:38]=2)[N:30]=[C:29]1[C:40]1[C:44]([NH2:45])=[CH:43][NH:42][N:41]=1.C(N(CC)CC)C.C1(C(Cl)=O)CC1.[OH-].[K+].[Cl-].[NH4+]>O1CCCC1>[NH:30]1[C:31]2[C:39](=[CH:38][C:37]3[CH2:36][CH2:35][CH2:34][C:33]=3[CH:32]=2)[N:28]=[C:29]1[C:40]1[C:44]([NH:45][C:4]([CH:26]2[CH2:7][CH2:25]2)=[O:3])=[CH:43][NH:42][N:41]=1

参加物

8

反応物 6

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 178508051HCID 178508051、化合物HCID 178522444HCID 178522444、化合物

生成物 1

HCID 178522415HCID 178522415、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

By proceeding in a similar manner to Example 258(a) above but (i) treating a solution of 3-(1,5,6,7-tetrahydro-1,3-diaza-s-indacen-2-yl)-1H-pyrazol-4-ylamine [310 mg, Example 256(b)] and triethylamine (4 eq) in tetrahydrofuran (15 mL) with cyclopropanecarbonyl chloride (4 eq), (ii) stirring the reaction mixture at 60° C. for 2 hours, (iii) treating the resulting bis-acylated product with methanolic potassium hydroxide (20 mL, 10.05 g KOH) at 40° C. for 1 hour followed by treatment with aqueous ammonium chloride (200 mL), (iii) extracting this mixture three times with ethyl acetate (100 mL), (iv) evaporating the combined extracts and (v) chromatographing the residue on silica gel (ethyl acetate/gradient of 50-0% heptane) there was prepared cyclopropanecarboxylic acid [3-(1,5,6,7-tetrahydro-1,3-diaza-s-indacen-2-yl)-1H-pyrazol-4-yl]amide (50 mg) as a yellow solid. LC-MS (Method E) RT=2.05 minutes, 308 (M+H)+.

後処理

  1. extractionextracting this mixture three times with ethyl acetate (100 mL), (iv)
  2. customevaporating the combined extracts and (v) chromatographing the residue on silica gel (ethyl acetate/gradient of 50-0% heptane) there
  3. customwas prepared cyclopropanecarboxylic acid [3-(1,5,6,7-tetrahydro-1,3-diaza-s-indacen-2-yl)-1H-pyrazol-4-yl]amide (50 mg) as a yellow solid

出典と根拠

ORDレコード
ord-700ab96b803142cc9a16ff22c6550e8f
出典データセット
uspto-grants-2012_10
特許番号
US08288425B2

反応ノート

読み込み中…