Hydrochloric Acid → Gdc-0623

HRID 1500712노트

반응식

HRID 1500712 반응식
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:25]=[N:26][CH:27]=2)[C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=1[F:24])=[O:9])=C.Cl>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:25]=[N:26][CH:27]=2)[C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=1[F:24])=[O:9]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 591401665-(2-Fluoro-4-iodophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-vinyloxyethoxy)-amide

생성물 1

HCID 42642654Gdc-0623수율 92.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a suspension of 5-(2-fluoro-4-iodophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-vinyloxyethoxy)-amide (2.87 g, 5.95 mmol) in methanol (45 mL) was added aqueous hydrochloric acid (11.9 mL, 1M, 11.9 mmol). The reaction mixture was stiffed at room temperature for 45 minutes during which time the solids dissolved. The reaction mixture was concentrated in vacuo to remove the methanol. The resultant solution was diluted with 1:1 tert-butylmethylether:ethyl acetate (20 mL) and aqueous saturated sodium hydrogen carbonate solution (20 mL) added. The resultant mixture was sonicated until a precipitate formed and the precipitate was collected by filtration and dried in vacuo at 45° C. to yield the title compound as a yellow solid (2.5 g, 92%). LCMS (Method A): RT=5.58 min, M+H+=457. 1H NMR (DMSO-d6, 400 MHz) 8.05 (1 H, s), 7.58 (1 H, dd, J=10.69, 1.92 Hz), 7.43 (1 H, s), 7.39 (1 H, d, J=9.33 Hz), 7.31-7.28 (1 H, m), 6.89 (1 H, d, J=9.31 Hz), 6.34 (1 H, t, J=8.68 Hz), 4.64 (1 H, s), 3.64 (2 H, t, J=4.78 Hz), 3.46 (2 H, m).

후처리

  1. dissolutionthe solids dissolved
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove the methanol
  4. additionThe resultant solution was diluted with 1:1 tert-butylmethylether
  5. additionethyl acetate (20 mL) and aqueous saturated sodium hydrogen carbonate solution (20 mL) added
  6. customThe resultant mixture was sonicated until a precipitate
  7. customformed
  8. filtrationthe precipitate was collected by filtration
  9. customdried in vacuo at 45° C.

출처 및 근거

ORD 기록
ord-2725cd572ed3465a9524ed93e2c4f414
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206174B2

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