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

HRID 2234317ノート

反応式

HRID 2234317 の反応式
[CH:1]1([N:6]2[CH2:16][C:15]([CH3:18])([CH3:17])[C:14](=[O:19])[N:13]([CH3:20])[C:12]3[C:7]2=[N:8][C:9]([NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][C:23]=2[O:31][CH3:32])=[N:10][CH:11]=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:33]1([CH:38]2[CH2:43][CH2:42][CH:41]([NH2:44])[CH2:40][CH2:39]2)[CH2:37][CH2:36][CH2:35][CH2:34]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:1]1([N:6]2[CH2:16][C:15]([CH3:17])([CH3:18])[C:14](=[O:19])[N:13]([CH3:20])[C:12]3[C:7]2=[N:8][C:9]([NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([NH:44][CH:41]4[CH2:40][CH2:39][CH:38]([N:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)[CH2:43][CH2:42]4)=[O:28])=[CH:24][C:23]=2[O:31][CH3:32])=[N:10][CH:11]=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

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 21882596Cyclohexanamine, 4-(1-pyrrolidinyl)-, trans-(9CI)2 回HCID 426107874-(9-cyclopentyl-5,7,7-trimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid2 回

生成物 1

HCID 581539494-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-3-methoxy-N-(4-pyrrolidin-1-ylcyclohexyl)benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-3-methoxy-benzoic acid (Intermediate 236; 83 mg, 0.19 mmol) in DMF (3 mL) was added a solution of 4-pyrrolidin-1-ylcyclohexan-1-amine (Intermediate 237; 78 mg, 0.46 mmol). DIPEA (100 uL, 0.57 mmol) was added, followed by HATU (107 mg, 0.28 mmol). The resultant mixture was stirred at ambient temperature for 2 hours. The reaction mixture was evaporated to a gum, which was partitioned between DCM (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL). The organic phase was separated by gravity elution through a PTFE filter cup and evaporated to an amber gum which was purified by base modified reverse phase preparative HPLC to yield the title compound as an off white solid (34 mg, 30%).

後処理

  1. customThe reaction mixture was evaporated to a gum, which
  2. customwas partitioned between DCM (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL)
  3. customThe organic phase was separated by gravity elution through a PTFE
  4. filtrationfilter cup
  5. customevaporated to an amber gum which
  6. customwas purified by base modified reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-9c9b03c6ca4047c1bdc41ef047b160e9
出典データセット
uspto-grants-2010_05
特許番号
US07709471B2

反応ノート

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