Triethylamine → (5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)-(3-morpholin-4-ylazetidin-1-yl)methanone

HRID 1945614노트

반응식

HRID 1945614 반응식
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:10]=[C:9]([C:11]([OH:13])=O)[S:8][C:6]=2[N:7]=1.C(Cl)(=O)C(Cl)=O.CCN(CC)CC.[NH:33]1[CH2:36][CH:35]([N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH2:34]1>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:10]=[C:9]([C:11]([N:33]3[CH2:36][CH:35]([N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)[CH2:34]3)=[O:13])[S:8][C:6]=2[N:7]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 134019734-(Azetidin-3-yl)morpholineHCID 866482365-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carboxylic acid

생성물 1

HCID 59606054(5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)-(3-morpholin-4-ylazetidin-1-yl)methanone수율 63.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carboxylic acid (301 mg, 1.0 mmol) in DCM (6 mL) was added oxalyl chloride (847 μL, 10.00 mmol) and the resulting mixture allowed to stir at r.t. for 1 h then concentrated in vacuo and azeotroped with toluene. The resulting yellow solid was suspended in a mixture of DCM (6 mL) and NEt3 (418 μL, 3.00 mmol) at 0° C. before the addition of 4-azetidin-3-ylmorpholine (142 mg, 1.00 mmol). The resulting mixture was warmed to r.t. after 1 h then stirred for a further 30 min. The reaction mixture was partitioned between DCM and H2O, the organic phase dried (Na2SO4) and concentrated in vacuo. The resulting residue was triturated with EtOAc and dried in vacuo affording the title compound as an off-white solid (269 mg, 63%). LCMS (method H): RT 2.19 min [M+H]+ 425.3

후처리

  1. concentrationthen concentrated in vacuo
  2. customazeotroped with toluene
  3. temperatureThe resulting mixture was warmed to r.t. after 1 h
  4. stirringthen stirred for a further 30 min
  5. customThe reaction mixture was partitioned between DCM and H2O
  6. dry with materialthe organic phase dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was triturated with EtOAc
  9. customdried in vacuo

출처 및 근거

ORD 기록
ord-ec143ac88940484291679cfe76efb5e2
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394796B2

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