Cyanamide → [4-Amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl][4-(1-pyrrolidinyl)phenyl]methanone

HRID 10801

반응식

HRID 10801 반응식
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=[C:2]=[S:3].[N:17]#[C:18][NH2:19].CC(C)([O-])C.[K+].Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1)=[O:29]>C(#N)C.C(O)(C)(C)C>[NH2:17][C:18]1[N:19]=[C:2]([NH:1][C:4]2[CH:5]=[CH:6][C:7]([N:10]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]3)=[CH:8][CH:9]=2)[S:3][C:27]=1[C:28]([C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1)=[O:29]

참가 물질

7

반응물 4

HCID 9864CyanamideHCID 36817854-(Pyrrolidin-1-yl)phenacyl bromideHCID 137183971-(4-Isothiocyanatophenyl)-4-methylpiperazineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 21958913[4-Amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl][4-(1-pyrrolidinyl)phenyl]methanone수율 4%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6386tert-Butanol용매

실험 절차

tert-Butanol (4 mL) and then 1-(4-isothiocyanatophenyl)-4-methyl piperazine (of Example 1; 219 mg, 1 mmol) were added to a solution of cyanamide (44 mg, 1.05 mmol) in acetonitrile (5 mL). Potassium t-butoxide (1 M in tert-butanol; 1 mL, 1 mmol) was added and the solution was stirred for 30 min. 2-Bromo-1-[4-(1-pyrrolidinyl)phenyl]ethanone (257 mg, 1 mmol) (Lancaster) was added, and the solution was stirred at room temperature for 2 days. The yellow-brown solid was filtered off and washed with cold acetonitrile, water and then cold acetonitrile (weight of solid: 271 mg). A portion of this crude product (50 mg) was purified by chromatography (10% methanol/dichloromethane) to give [4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl][4-(1-pyrrolidinyl) phenyl]methanone (18.5 mg).

후처리

  1. stirringthe solution was stirred at room temperature for 2 days
  2. filtrationThe yellow-brown solid was filtered off
  3. washwashed with cold acetonitrile, water
  4. customA portion of this crude product (50 mg) was purified by chromatography (10% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-b17a0c7b6d284d0a959d2f696bb214cf
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094896B2

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