Triethylamine → HCID 178522415, 화합물

HRID 2064623노트

반응식

HRID 2064623 반응식
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

참가 물질

8

반응물 6

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 178508051HCID 178508051, 화합물HCID 178522444HCID 178522444, 화합물

생성물 1

HCID 178522415HCID 178522415, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-700ab96b803142cc9a16ff22c6550e8f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288425B2

반응 노트

불러오는 중…