Chloride → 6-Amino-1-(3-cyclopentyloxy-4-methoxy-benzyl)-5-(2-(4-methoxybenzyloxy)-2-methyl-propionylamino)-2-thiouracil

HRID 2227360노트

반응식

HRID 2227360 반응식
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8][C:9]([CH3:14])([CH3:13])[C:10](Cl)=[O:11])=[CH:5][CH:4]=1.[NH2:17][C:18]1[C:19](=[O:41])[NH:20][C:21](=[S:40])[N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:27]=2)[C:23]=1[NH2:24].[Cl-]>C1COCC1>[NH2:24][C:23]1[N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:27]=2)[C:21](=[S:40])[NH:20][C:19](=[O:41])[C:18]=1[NH:17][C:10](=[O:11])[C:9]([O:8][CH2:7][C:6]1[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([CH3:14])[CH3:13]

참가 물질

5

반응물 3

HCID 312ChlorideHCID 184734541-(3-Cyclopentyloxy-4-methoxy-benzyl)-5,6-diamino-2-thiouracilHCID 184736132-(4-Methoxybenzyloxy)-2-methyl-propionyl chloride

생성물 1

HCID 184735306-Amino-1-(3-cyclopentyloxy-4-methoxy-benzyl)-5-(2-(4-methoxybenzyloxy)-2-methyl-propionylamino)-2-thiouracil

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution with 2.91 g (12 mM) of crude 2-(4-methoxybenzyloxy)-2-methyl-propionyl chloride in 9 ml of THF was added within 90 min to a stirred suspension with 3.62 g (10 mM) of 5,6-diamino-1-(3-cyclopentyloxy-4-methoxy-benzyl)-2-thiouracil. After 20 hr another 485 mg of chloride in 5 ml of THF was added within 30 min. After a further 3 hr the solid was filtered off and the solution evaporated in vacuo to dryness. The residue was dissolved in ethyl acetate, extracted with sodium bicarbonate solution and the organic phase evaporated in vacuo to dryness. The residue was crystallized from methanol: 1.71 g (30.1%) of amide with mp 172-184° C.

후처리

  1. filtrationAfter a further 3 hr the solid was filtered off
  2. customthe solution evaporated in vacuo to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. extractionextracted with sodium bicarbonate solution
  5. customthe organic phase evaporated in vacuo to dryness
  6. customThe residue was crystallized from methanol

출처 및 근거

ORD 기록
ord-683fd301326b406490c46550db445777
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06413975B1

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