반응 #42972

반응 방정식

ammonia

Thiophosgene

solution

2-(4-Amino-6,8-dimethoxy-isoquinolin-1-ylmethyl)-isoindole-1,3-dione

DIEA

Bromopyruvic acid

→

title compound

수율 75.0%

2-[1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-6,8-dimethoxy-isoquinolin-4-ylamino]-thiazole-4-carboxylic acid

수율 75.0%

용매

THF

반응 조건

후처리

1. 1
   추출extracted with EtOAc
2. 2
   건조Organics were dried (MgSO4)
3. 3
   농축concentrated
4. 4
   workup.DISSOLUTIONThe resulting crude thiourea was dissolved in THF (5 mL)
5. 5
   workup.STIRRINGthe reaction stirred for 2 h
6. 6
   기타Purification by silica gel chromatography (10% MeOH/CHCl3)

실험 절차

Thiophosgene (146 μL, 1.92 mmol) was added to a solution of Example 45C (580 mg, 1.6 mmol) and DIEA (670 μL) in THF (10 mL). After stirring for 1 h, the reaction was poured over aqueous ammonia and extracted with EtOAc. Organics were dried (MgSO4) and concentrated. The resulting crude thiourea was dissolved in THF (5 mL). Bromopyruvic acid (320 mg, 1.92 mmol) was added, and the reaction stirred for 2 h. Purification by silica gel chromatography (10% MeOH/CHCl3) gave 590 mg (75%) of the title compound as a tan solid. H1-NMR (MeOD-d4): δ 9.95 (br s, 1H), 8.81 (br s, 1H), 7.87-7.96 (m, 4H), 7.60 (br s, 1H), 7.14 (s, 1H), 6.86 (s, 1H), 5.41 (s, 2H), 4.09 (s, 3H), 3.94 (s, 3H). MS (ES) (M+H) calc'd for C24H18N4O6S, 491; found 491.

출처