Potassium Carbonate → Thiazolo[4,5-c]pyridine-6-carboxylic acid,2-[(1-methylethyl)amino]-,methyl ester

HRID 1452967노트

반응식

HRID 1452967 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([NH:11][CH:12]([CH3:14])[CH3:13])[S:10][C:4]=2[CH:3]=1.[C:15]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:44]([O-:47])([O-])=[O:45].[K+].[K+]>CO.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:12]([NH:11][C:9]1[S:10][C:4]2[CH:3]=[C:2]([C:44]([O:47][CH3:15])=[O:45])[N:7]=[CH:6][C:5]=2[N:8]=1)([CH3:14])[CH3:13]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 575272276-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine

생성물 1

HCID 57527243Thiazolo[4,5-c]pyridine-6-carboxylic acid,2-[(1-methylethyl)amino]-,methyl ester수율 301.2%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 6-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine (0.24 g, 1.05 mmol, 1.0 eq.), Pd(OAc)2 (0.0313 g, 0.139 mmol, 0.1 eq.), 1,3-bis(diphenylphosphino)propane (0.0443 g, 0.107 mmol, 0.1 eq.) and K2CO3 (0.2214 g, 1.60 mmol, 1.5 eq.) in MeOH (2.6 mL) and DMF (1.3 mL) was stirred under an atmosphere of CO inside a bomb (40 psi) at 91° C. overnight. After cooling to room temperature, the reaction mixture was filtered through Celite and rinsed with MeOH. The filtrate was concentrated in vacuo, diluted with EtOAc and water. The layers were separated, and the organic layer was washed with brine and 10% aqueous LiCl, dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with CH2Cl2:MeOH (10:0.3) to give methyl 2-(isopropylamino)thiazolo[4,5-c]pyridine-6-carboxylate as a white solid (0.081 g, 31% yield).

후처리

  1. filtrationthe reaction mixture was filtered through Celite
  2. washrinsed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiondiluted with EtOAc and water
  5. customThe layers were separated
  6. washthe organic layer was washed with brine and 10% aqueous LiCl
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with CH2Cl2:MeOH (10:0.3)

출처 및 근거

ORD 기록
ord-b4d6cabc7d6349d6af2901154b2e17e2
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473784B2

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