Diisopropylethylamine → Tert-butyl 3-(6-(6-(4-hydroxybenzylamino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-ylamino)nicotinamido)-2,2-dimethylpropylcarbamate

HRID 1485655ノート

反応式

HRID 1485655 の反応式
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:40]=[CH:39][C:14]([CH2:15][NH:16][C:17]2[N:22]=[C:21]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[N:20]=[C:19]([NH:29][C:30]3[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][N:31]=3)[CH:18]=2)=[CH:13][CH:12]=1.[C:41]([O:45][C:46](=[O:54])[NH:47][CH2:48][C:49]([CH3:53])([CH3:52])[CH2:50][NH2:51])([CH3:44])([CH3:43])[CH3:42].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[OH:10][C:11]1[CH:40]=[CH:39][C:14]([CH2:15][NH:16][C:17]2[N:22]=[C:21]([O:23][CH2:24][C:25]([F:28])([F:26])[F:27])[N:20]=[C:19]([NH:29][C:30]3[CH:38]=[CH:37][C:33]([C:34]([NH:51][CH2:50][C:49]([CH3:53])([CH3:52])[CH2:48][NH:47][C:46](=[O:54])[O:45][C:41]([CH3:44])([CH3:42])[CH3:43])=[O:35])=[CH:32][N:31]=3)[CH:18]=2)=[CH:13][CH:12]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 4114359tert-butyl N-(3-amino-2,2-dimethylpropyl)carbamateHCID 866793196-((6-((4-Hydroxybenzyl)amino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-yl)amino)nicotinic acid

生成物 1

HCID 86679318Tert-butyl 3-(6-(6-(4-hydroxybenzylamino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-ylamino)nicotinamido)-2,2-dimethylpropylcarbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

iPr2NEt (0.5 mL) was added into a solution of 6-((6-((4-hydroxybenzyl)amino)-2-(2,2,2-trifluoroethoxyl)pyrimidin-4-yl)amino)nicotinic acid (340 mg), tert-butyl(3-amino-2,2-dimethylpropyl)carbamate (316 mg) and TBTU (501 mg) in THF (10 mL). The reaction was stirred at room temperature for 16 hours before being quenched by water (10 mL). The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic phase was dried over MgSO4 and concentrated under vacuum to give the crude product, tert-butyl 3-(6-(6-(4-hydroxybenzylamino)-2-(2,2,2-trifluoroethoxyl)pyrimidin-4-ylamino)nicotinamido)-2,2-dimethylpropylcarbamate, which was purified by silica gel chromatography.

後処理

  1. custombefore being quenched by water (10 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-bf1bddda50314603aa0b04ff49a56a74
出典データセット
uspto-grants-2016_08
特許番号
US09422311B2

反応ノート

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