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Trifluoroacetic acid → 2-({[(8-hydroxy-1,6-naphthyridin-7-yl)carbonyl]amino}methyl)-1H-benzimidazol-1-ium Trifluoroacetate

HRID 896282
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HRID 896282 반응식
ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(O[C:17]([C:19]1[C:24]([CH2:25][N:26]([CH2:37][C:38]([O:40]C)=O)S(C2C=CC(C)=CC=2)(=O)=O)=[CH:23][CH:22]=[CH:21][N:20]=1)=[O:18])(C)C.C(N(C(C)C)CC)(C)C.O.[Cl-].[Cl-].[NH3+:54][CH2:55][C:56]1[NH2+:60][C:59]2[CH:61]=[CH:62][CH:63]=[CH:64][C:58]=2[N:57]=1.[C:65]([OH:71])([C:67]([F:70])([F:69])[F:68])=[O:66]>CN(C=O)C>[F:68][C:67]([F:70])([F:69])[C:65]([O-:71])=[O:66].[OH:18][C:17]1[C:37]([C:38]([NH:54][CH2:55][C:56]2[NH2+:60][C:59]3[CH:61]=[CH:62][CH:63]=[CH:64][C:58]=3[N:57]=2)=[O:40])=[N:26][CH:25]=[C:24]2[C:19]=1[N:20]=[CH:21][CH:22]=[CH:23]2
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참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 43835646Benzimidazol-2-ylmethylamine, oxamethane, chloride, chlorideHCID 599831603-{[Methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-pyridine-2-carboxylic Acid Isopropyl Ester

생성물 1

HCID 22350044
2-({[(8-hydroxy-1,6-naphthyridin-7-yl)carbonyl]amino}methyl)-1H-benzimidazol-1-ium Trifluoroacetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Triphosgene (0.556 g, 1.87 mmol) was added over 20 mins to a solution of the acid from Step 1. (0.89 g, 4.68 mmol) and diisopropylethylamine 3.26 ml, 18.7 mmol) in DMF (22 ml) at 0° C. The dark solution was allowed to warm to room temperature and stirred a further 1 hr. 2-(ammoniomethyl)-1H-benzimidazol-1-ium dichloride hydrate (25.0 mg, 1.05 mmol) was treated with a portion of the above solution (0.58 ml, 0.07 mmol) and the resulting mixture was stirred at room temperature for 16 hrs. The solution was treated with TFA (0.025 ml) and purified by preparative HPLC. (Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) (available from Waters) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min) to afford the trifluoroacetate salt of the title compound after lyophilization.

후처리

  1. customat 0° C
  2. stirringthe resulting mixture was stirred at room temperature for 16 hrs
  3. custompurified by preparative HPLC
  4. wash(Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) (available from Waters) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min)

출처 및 근거

ORD 기록
ord-22dd52fbf50647fabf4cdd7503f820b4
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06919351B2

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