6-Formyl-[1,5]naphthyridine-3-carbonitrile → HCID 178510297, 화합물

HRID 968724노트

반응식

HRID 968724 반응식
C(O[C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]=[C:16]3[S:20][C:19]([NH:21][CH2:22][C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[N:18][C:17]3=[O:28])[N:13]=2)[N:8]=[CH:7][C:6]=1[C:29]#[N:30])(C)C.C(O[Na])(C)=O.C(C1N=C2C(=CC=1)N=CC(C#N)=C2)=O>CC(O)=O>[O:28]=[C:17]1[C:16](=[CH:15][C:12]2[N:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:29]#[N:30])=[CH:5]3)[S:20][C:19]([NH:21][CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[N:18]1

참가 물질

5

반응물 3

HCID 587243016-Formyl-[1,5]naphthyridine-3-carbonitrileHCID 178418247HCID 178418247, 화합물HCID 178458710HCID 178458710, 화합물

생성물 1

HCID 178510297HCID 178510297, 화합물수율 21.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

To a mixture of 2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one one (34.0 mg, 0.16 mmol) (see Example 4), AcONa (160 mg, 1.95 mmol), and 6-formyl-[1,5]naphthyridine-3-carbonitrile (38.5 mg, 0.21 mmol) (prepared as described below) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 100° C. (oil bath) for 4.5 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water. The solid was then dissolved in DMF (1 mL) with heating and then poured into ice water, and filtered. The solid was washed with AcOEt and dried to give 6-{4-oxo-2-[(thiophen-2-ylmethyl)-amino]-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a dark brown solid (12.8 mg, 21.2%). HR-ES (+) m/e calcd for C18H11N5OS2 (M+H)+ 400.0297. found 400.0298.

후처리

  1. temperatureThe reaction mixture was then cooled to r.t.
  2. customtriturated with water
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. dissolutionThe solid was then dissolved in DMF (1 mL)
  6. temperaturewith heating
  7. additionpoured into ice water
  8. filtrationfiltered
  9. washThe solid was washed with AcOEt
  10. customdried

출처 및 근거

ORD 기록
ord-d56cb615fd744070ae77d0be09e10156
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304074B2

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