p-Toluenesulfonic acid monohydrate → HCID 25123685, compound

HRID 2234314Notes

Reaction equation

HRID 2234314 reaction equation
Cl[C:2]1[N:12]=[C:11]2[C:5]([NH:6][C:7](=[O:20])[C:8]([CH3:19])([CH3:18])[CH2:9][N:10]2[CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:43]=[CH:42][C:25]([C:26]([NH:28][CH:29]2[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]2)=[O:27])=[CH:24][C:23]=1[O:44][CH3:45].O.[C:47]1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)CC(O)C>[CH:13]1([N:10]2[CH2:9][C:8]([CH3:19])([CH3:18])[C:7](=[O:20])[N:6]([CH3:47])[C:5]3[C:11]2=[N:12][C:2]([NH:21][C:22]2[CH:43]=[CH:42][C:25]([C:26]([NH:28][CH:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[O:27])=[CH:24][C:23]=2[O:44][CH3:45])=[N:3][CH:4]=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 581540122-Chloro-9-cyclopentyl-7,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one2×HCID 68684708HCID 68684708, compound2×

Product 1

HCID 25123685HCID 25123685, compound

Reagents, catalysts & solvents 1

HCID 79104-Methyl-2-PentanolSolvent

Conditions

Temperature
90 °C

Procedure

10-chloro-2-cyclopentyl-4,4-dimethyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 127; 50 mg, 0.16 mmol) and tert-butyl 4-[(4-amino-3-methoxy-benzoyl)amino]piperidine-1-carboxylate (Intermediate 234; 85 mg, 0.24 mmol) were dissolved in 4-methyl-2-pentanol (1 mL) and p-toluenesulphonic acid monohydrate (44 mg, 0.32 mmol) added. The reaction mixture was heated at 90° C. by microwave irradiation for 20 minutes and then at 150° C. for a further 45 minutes.

Sources & evidence

ORD record
ord-5aecb5902e724282bc2bae75a21e7020
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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