5-(Chloromethyl)-1,2,3-trimethoxybenzene → HCID 178491928, 화합물

HRID 77517

반응식

HRID 77517 반응식
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([NH:12][C:13]([C:15]1[C:20]([NH2:21])=[N:19][C:18]([NH2:22])=[C:17]([Cl:23])[N:16]=1)=[O:14])=[NH:11])[CH2:2]2.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35])[CH2:29]Cl>CN(C=O)C>[Cl-:23].[NH2:21][C:20]1[C:15]([C:13]([N:12]=[C:10]([NH2:11])[NH:9][CH:3]2[CH:4]3[CH2:7][CH2:8][N+:1]([CH2:29][C:28]4[CH:31]=[C:32]([O:36][CH3:37])[C:33]([O:34][CH3:35])=[C:26]([O:25][CH3:24])[CH:27]=4)([CH2:6][CH2:5]3)[CH2:2]2)=[O:14])=[N:16][C:17]([Cl:23])=[C:18]([NH2:22])[N:19]=1

참가 물질

4

반응물 2

HCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 178512394HCID 178512394, 화합물2회

생성물 1

HCID 178491928HCID 178491928, 화합물수율 42%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-N′-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidine (Intermediate 4, 152 mg, content ca. 66%, 0.30 mmol) and 3,4,5-trimethoxybenzyl chloride (Aldrich, 77 mg, 0.36 mmol) is stirred in DMF (1 mL) at r.t. for ca. 18 h. The crude mixture is purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient). The product thus obtained is triturated with a mixture of diethyl ether (4 mL) and methanol (1.5 mL), collected by filtration and dried under vacuum at 70° C. Further trituration with water (0.3 mL), filtration and drying under vacuum at 70° C. yields the title compound (35 mg).

후처리

  1. customThe crude mixture is purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient)
  2. customThe product thus obtained
  3. customis triturated with a mixture of diethyl ether (4 mL) and methanol (1.5 mL)
  4. filtrationcollected by filtration
  5. customdried under vacuum at 70° C
  6. filtrationFurther trituration with water (0.3 mL), filtration
  7. customdrying under vacuum at 70° C.

출처 및 근거

ORD 기록
ord-580fc6527acf4792bf8acfdf329ed787
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841309B2

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