4-Methyl-2-Pentanol → 4-[(2-cyclopentyl-4,4-diethyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamide

HRID 2234318

Reaction equation

HRID 2234318 reaction equation
Cl[C:2]1[N:12]=[C:11]2[C:5]([N:6]([CH3:23])[C:7](=[O:22])[C:8]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:9][N:10]2[CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:36][C:37]1[CH:55]=[CH:54][C:40]([C:41]([NH:43][CH2:44][C:45]([CH3:53])([CH3:52])[CH2:46][N:47]2[CH2:51][CH2:50][CH2:49][CH2:48]2)=[O:42])=[CH:39][C:38]=1[O:56][CH3:57].CC(C)CC(O)C>CO>[CH:13]1([N:10]2[CH2:9][C:8]([CH2:20][CH3:21])([CH2:18][CH3:19])[C:7](=[O:22])[N:6]([CH3:23])[C:5]3[C:11]2=[N:12][C:2]([NH:36][C:37]2[CH:55]=[CH:54][C:40]([C:41]([NH:43][CH2:44][C:45]([CH3:52])([CH3:53])[CH2:46][N:47]4[CH2:51][CH2:50][CH2:49][CH2:48]4)=[O:42])=[CH:39][C:38]=2[O:56][CH3:57])=[N:3][CH:4]=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 79104-Methyl-2-PentanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 686858814-amino-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamide2×HCID 8661756310-Chloro-2-cyclopentyl-4,4-diethyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one2×

Product 1

HCID 686849234-[(2-cyclopentyl-4,4-diethyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamideYield 27.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

10-chloro-2-cyclopentyl-4,4-diethyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one (Intermediate 250; 111 mg, 0.33 mmol), p-toluenesulphonic acid monohydrate (155 mg, 0.81 mmol) and 4-amino-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamide (Intermediate 206; 100 mg, 0.33 mmol) were added to 4-methyl-2-pentanol (7 mL). The reaction was heated at 120° C. over the weekend. The sample was transferred to an SCX cartridge (10 g) pre-wet with methanol, then washed with methanol and eluted with methanolic ammonia. 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 (55 mg, 27%).

Workup

  1. washwashed with methanol
  2. washeluted with methanolic ammonia
  3. additionProduct containing fractions
  4. customevaporated
  5. customthe resultant material purified by base modified reverse phase preparative HPLC

Sources & evidence

ORD record
ord-60b4843b9356418ca573b23f27335ab6
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Linked notes

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