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Diisopropylethylamine → 2-chloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-5-methoxy-N-[(3R)-1-methylpyrrolidin-3-yl]benzamide

HRID 2234313
ノート
印刷プレビュー

反応式

HRID 2234313 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]2[N:22]=[C:21]3[C:15]([N:16]([CH3:29])[C:17](=[O:28])[CH2:18][CH2:19][N:20]3[CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:14][N:13]=2)[C:8]([O:30][CH3:31])=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.Cl.[CH3:34][N:35]1[CH2:39][CH2:38][C@@H:37]([NH2:40])[CH2:36]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CO>[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]2[N:22]=[C:21]3[C:15]([N:16]([CH3:29])[C:17](=[O:28])[CH2:18][CH2:19][N:20]3[CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:14][N:13]=2)[C:8]([O:30][CH3:31])=[CH:7][C:3]=1[C:4]([NH:40][C@@H:37]1[CH2:38][CH2:39][N:35]([CH3:34])[CH2:36]1)=[O:6]
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 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53256048(3R)-1-Methyl-3-PyrrolidinaMine hydrochloride2 回HCID 686856472-Chloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-5-methoxy-benzoic acid2 回

生成物 1

HCID 68685379
2-chloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-5-methoxy-N-[(3R)-1-methylpyrrolidin-3-yl]benzamide
収率 64.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

2-chloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-5-methoxy-benzoic acid (Intermediate 231; 100 mg, 0.224 mmol), (3R)-1-methylpyrrolidin-3-amine di Hydrochloride (Intermediate 184; 40 mg, 0.235 mmol), HATU (94 mg, 0.246 mmol) and DIPEA (195 μL, 1.12 mmol) were combined in DMF (3 mL) and stirred at room temperature overnight. The reaction mixture was added to an SCX-2 column (5 g) pre-wet with MeOH (2 column volumes), flushed with MeOH (2 column volumes) and eluted with 2M ammonia in MeOH. Product containing fractions were combined and evaporated and the resultant material purified by base modified reverse phase preparative HPLC to yield the title compound as a white solid (76 mg, 64%).

後処理

  1. customflushed with MeOH (2 column volumes)
  2. washeluted with 2M ammonia in MeOH
  3. additionProduct containing fractions
  4. customevaporated
  5. customthe resultant material purified by base modified reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-5f0d4ed4365344fa9befbeed1e3a5132
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07709471B2

反応ノート

読み込み中…

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