Cyclopentylamine → 1-tert-butyl 3-methyl 4-((1-(cyclopentylcarbamoyl)cyclopentylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate

HRID 1968237Notes

Reaction equation

HRID 1968237 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][C:16]([CH2:17][NH:18][C:19]3([C:24](O)=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:11]2[C:10]([C:27]([O:29][CH3:30])=[O:28])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=N[C:41]2[CH:42]=[CH:43][CH:44]=[N:45][C:40]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CCCC1.CN1CCOCC1>C1COCC1>[CH:40]1([NH:45][C:24]([C:19]2([NH:18][CH2:17][C:16]3[CH:15]=[CH:14][N:13]=[C:12]4[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:9]=[C:10]([C:27]([O:29][CH3:30])=[O:28])[C:11]=34)[CH2:20][CH2:21][CH2:22][CH2:23]2)=[O:25])[CH2:41][CH2:42][CH2:43][CH2:44]1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58293428HCID 58293428, compound

Product 1

HCID 582934711-tert-butyl 3-methyl 4-((1-(cyclopentylcarbamoyl)cyclopentylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
43 °C

Procedure

To 1-((1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methylamino)cyclopentanecarboxylic acid was added THF (2 mL), HATU (94 mg, 0.246 mmol), cyclopentanamine (70.0 mg, 0.822 mmol) and 4-methylmorpholine (83 mg, 0.822 mmol). The suspension was stirred at 43° C. for 36 h to afford the title compound, which was used in the next step without further purification. [M+H] calc'd for C26H36N4O5, 485; found, 485.4.

Sources & evidence

ORD record
ord-f615cd5edd804f338d2546806c124892
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

Loading…