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

HRID 896282
ノート
印刷プレビュー

反応式

HRID 896282 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-22dd52fbf50647fabf4cdd7503f820b4
出典データセット
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06919351B2

反応ノート

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