p-Toluenesulfonic acid monohydrate → 7-(9'-cyclopentyl-5'-methyl-6'-oxo-5',6',8',9'-tetrahydrospiro[cyclopropane-1,7'-pyrimido[5,4-b][1,4]diazepine]-2'-ylamino)-N-(1-methyl-4-piperidyl)benzo[1,3]dioxole-4-carboxamide

HRID 2234332Notes

Reaction equation

HRID 2234332 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH3:21])[C:7](=[O:20])[C:8]3([CH2:19][CH2:18]3)[CH2:9][N:10]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1.[NH2:22][C:23]1[C:28]2[O:29][CH2:30][O:31][C:27]=2[C:26]([C:32]([NH:34][CH:35]2[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]2)=[O:33])=[CH:25][CH:24]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)CC(O)C>[CH:13]1([N:10]2[CH2:9][C:8]3([CH2:19][CH2:18]3)[C:7](=[O:20])[N:6]([CH3:21])[C:5]3[CH:4]=[N:3][C:2]([NH:22][C:23]4[C:28]5[O:29][CH2:30][O:31][C:27]=5[C:26]([C:32]([NH:34][CH:35]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]5)=[O:33])=[CH:25][CH:24]=4)=[N:12][C:11]2=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 579699392-chloro-9-cyclopentyl-8,9-dihydro-5-methylspiro[5H-pyrimido[4,5-b][1,4]diazepine-7,1'-cyclopropan]-6(7H)-one2×HCID 686813937-amino-N-(1-methyl-4-piperidyl)benzo[1,3]dioxole-4-carboxamide2×

Product 1

HCID 686822177-(9'-cyclopentyl-5'-methyl-6'-oxo-5',6',8',9'-tetrahydrospiro[cyclopropane-1,7'-pyrimido[5,4-b][1,4]diazepine]-2'-ylamino)-N-(1-methyl-4-piperidyl)benzo[1,3]dioxole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 79104-Methyl-2-PentanolSolvent

Conditions

Temperature
160 °C

Procedure

To 2′-chloro-9′-cyclopentyl-5′-methyl-8′,9′-dihydrospiro[cyclopropane-1,7′-pyrimido[4,5-b][1,4]diazepin]-6′(5′H)-one (Intermediate 130; 108 mg, 0.35 mmol) and 7-amino-N-(1-methylpiperidin-4-yl)benzo[d][1,3]dioxole-4-carboxamide (Intermediate 223; 98 mg, 0.35 mmol) in 4-methyl-2-pentanol (3 mL) was added p-toluenesulphonic acid monohydrate (139 mg, 0.73 mmol) and the reaction mixture heated at 160° C. by microwave irradiation for 1 hour.

Sources & evidence

ORD record
ord-98c037fde1a14fecabe6d8f27970e269
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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