Trifluoroacetic acid → 4-(2-(pyridin-4-yl)pyrrolidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)quinazoline-7-sulfonamide

HRID 1473694ノート

反応式

HRID 1473694 の反応式
COC1C=C(OC)C=CC=1C[N:6]([C:21]1[S:25][N:24]=[CH:23][N:22]=1)[S:7]([C:10]1[CH:19]=[C:18]2[C:13]([C:14](=O)[NH:15][CH:16]=[N:17]2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C1CCN2C(=NCCC2)CC1.[NH:70]1[CH2:74][CH2:73][CH2:72][CH:71]1[C:75]1[CH:80]=[CH:79][N:78]=[CH:77][CH:76]=1.C(O)(C(F)(F)F)=O>C(#N)C.C(OCC)(=O)C>[N:78]1[CH:79]=[CH:80][C:75]([CH:71]2[CH2:72][CH2:73][CH2:74][N:70]2[C:14]2[C:13]3[C:18](=[CH:19][C:10]([S:7]([NH:6][C:21]4[S:25][N:24]=[CH:23][N:22]=4)(=[O:9])=[O:8])=[CH:11][CH:12]=3)[N:17]=[CH:16][N:15]=2)=[CH:76][CH:77]=1

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27716644-(Pyrrolidin-2-yl)pyridine2 回HCID 136409075N-(2,4-dimethoxybenzyl)-4-oxo-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroquinazoline-7-sulfonamide

生成物 1

HCID 866877784-(2-(pyridin-4-yl)pyrrolidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)quinazoline-7-sulfonamide

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

To a solution of N-(2,4-dimethoxybenzyl)-4-oxo-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroquinazoline-7-sulfonamide (0.611 g, 1.330 mmol) and BOP (0.765 g, 1.729 mmol) in acetonitrile (6.65 ml) was added DBU (0.301 ml, 1.995 mmol). The reaction was stirred for 10 minutes at 40° C. 4-(pyrrolidin-2-yl)pyridine (0.272 ml, 1.995 mmol) was added and the reaction was stirred for 8 hours at 40° C. 4-(pyrrolidin-2-yl)pyridine (0.272 ml, 1.995 mmol) was added and the reaction was stirred for four hours at 40° C. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 40 g, gradient elution 0-10% MeOH:DCM). The material was dissolved in DCM and TFA (0.2 ml, 2.60 mmol) was added. The reaction was stirred for one hour at room temperature. The reaction was concentrated and purified via column chromatography (RediSep Gold 12 g, gradient elution 0-10% MeOH:DCM) to afford 4-(2-(pyridin-4-yl)pyrrolidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)quinazoline-7-sulfonamide as a light yellow solid. (ESI) 440.2 (M+H)+.

後処理

  1. stirringthe reaction was stirred for 8 hours at 40° C
  2. stirringthe reaction was stirred for four hours at 40° C
  3. washwashed with water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe material was purified via column chromatography (RediSep Gold 40 g, gradient elution 0-10% MeOH:DCM)
  9. dissolutionThe material was dissolved in DCM
  10. stirringThe reaction was stirred for one hour at room temperature
  11. concentrationThe reaction was concentrated
  12. custompurified via column chromatography (RediSep Gold 12 g, gradient elution 0-10% MeOH:DCM)

出典と根拠

ORDレコード
ord-f2e1fbdc4d634603afaef0a9bf9989ca
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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