Succinic Acid → 7-Chloro-6-[5-(cyclopropylmethyl-amino)-[1,3,4]thiadiazol-2-ylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine Succinate

HRID 1670566노트

반응식

HRID 1670566 반응식
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[CH2:13][S:14][C:15]1[S:16][C:17]([NH:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)=[N:18][N:19]=1.[C:25]([OH:32])(=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29]>C(O)C>[C:25]([OH:32])(=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29].[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[CH2:13][S:14][C:15]1[S:16][C:17]([NH:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)=[N:18][N:19]=1

참가 물질

4

반응물 2

HCID 1110Succinic AcidHCID 598223037-chloro-6-[5-(cyclopropylmethyl-amino)-[1,3,4]thiadiazol-2-ylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine

생성물 1

HCID 673355277-Chloro-6-[5-(cyclopropylmethyl-amino)-[1,3,4]thiadiazol-2-ylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine Succinate수율 100.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 3-tert-butoxycarbonyl-7-chloro-6-[5-(cyclopropylmethyl-amino)-[1,3,4]thiadiazol-2-ylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.082 g, 0.171 mmol) in anhydrous DCM (3.5 mL) at room temperature add trifluoroacetic acid (3.5 mL) and stir the solution at room temperature overnight. Concentrate in. vacuo and elute the residue through a SCX column (20 g). Dissolve the residue in DCM, load the solution on to a RediSep® column (12 g) and purify the crude mixture by preparative liquid chromatography (100:0 to 90:10 DCM/2M ammonia in methanol over 33 min; 35 mL/min) to afford 7-chloro-6-[5-(cyclopropylmethyl-amino)-[1,3,4]thiadiazol-2-ylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.051 g, 78%). MS (ES+) m/z: 381.1 (M+H)+. To a solution of 7-chloro-6-[5-(cyclopropylmethyl-amino)-[1,3,4]thiadiazol-2-ylthiomethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.044 g, 0.116 mmol) in absolute ethanol (5 mL), add succinic acid (0.014 g, 0.116 mmol). After acid dissolves, concentrate the reaction mixture in vacuo. Combine the residue with MTBE, concentrate in vacuo several times and dry under high vacuum at room temperature overnight to obtain the title compound (0.058 g, 100%) as a white foam. MS (ES+) m/z: 381.0 (M+H)+.

후처리

  1. dissolutionAfter acid dissolves
  2. concentrationconcentrate the reaction mixture in vacuo
  3. concentrationconcentrate in vacuo several times
  4. customdry under high vacuum at room temperature overnight

출처 및 근거

ORD 기록
ord-e71b2433897f413eaec0e2cc86e8e8e2
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994163B2

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