Propargyl alcohol → HCID 178432388, 화합물

HRID 2120768노트

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HRID 2120768 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH3:12])[N:8]=[CH:7][C:6]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:14])=[C:5]2[OH:24].[CH2:25]([OH:28])[C:26]#[CH:27].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:13]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[OH:24])=[CH:3][C:2]([C:27]#[C:26][CH2:25][OH:28])=[C:11]([CH3:12])[N:10]=3)=[O:14])=[CH:18][CH:19]=1

참가 물질

6

반응물 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 178432387HCID 178432387, 화합물

생성물 1

HCID 178432388HCID 178432388, 화합물수율 35.4%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of 6-bromo-N-(4-chlorobenzyl)-4-hydroxy-7-methyl[1,8]naphthyridine-3-carboxamide (0.244 g, 0.60 mmol), propargyl alcohol (0.047 g, 0.84 mmol), triethylamine (0.38 mL) and PdCl2(PPh3)2 (0.023 g, 0.03 mmol) in 3 mL DMF is heated to 90° C. for 2.5 h. The resulting solution is cooled and partitioned between EtOAc and water. The solid which formed is filtered and discarded. The aqueous layer is extracted with EtOAc (3×). The combined organic layers are washed with brine, dried and condensed. The crude product is chromatographed on silica (Biotage flash 40S, eluent 2% MeOH/CH2Cl2 then 3% MeOH/CH2Cl2. Fractions homogeneous by TLC are combined and condensed to yield 0.081 g (35%) of the desired product as a yellow solid. Physical characteristics are as follows: m.p. 279-281° C. (dec.); 1H NMR (DMSO-d6) δ13.19, 10.12, 8.64, 8.43, 7.38, 5.46, 4.54, 4.40, 2.71; IR (drift) 3194, 3065, 2944, 1645, 1597, 1566, 1522, 1488, 1418, 1357, 1257, 1208, 1015, 851, 809 cm−1; OAMS supporting ions at: ESI+ 381.9 ESI− 379.9; HRMS (FAB) calcd for C20H16CIN3O3 +H1 382.0958, found 382.0960.

후처리

  1. temperatureThe resulting solution is cooled
  2. custompartitioned between EtOAc and water
  3. customThe solid which formed
  4. filtrationis filtered
  5. extractionThe aqueous layer is extracted with EtOAc (3×)
  6. washThe combined organic layers are washed with brine
  7. customdried
  8. customcondensed
  9. customThe crude product is chromatographed on silica (Biotage flash 40S, eluent 2% MeOH/CH2Cl2
  10. customcondensed

출처 및 근거

ORD 기록
ord-9528541ec700436eaa8dd1855d4889d3
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693114B2

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