4-Amino-1-Boc-piperidine → 4-[3-(2H-tetrazol-5-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 502441Notes

Reaction equation

HRID 502441 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:20])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[NH:19][N:18]=[N:17][N:16]=3)[CH:10]=2)[CH2:3][CH2:2]1.N1C(C2C=C(C=CC=2)C(O)=O)=NN=N1.[C:35]([O:39][C:40](N1CCC(N)CC1)=[O:41])([CH3:38])([CH3:37])[CH3:36].Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.ClCCl>[C:35]([O:39][C:40]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:20])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[N:16]=[N:17][NH:18][N:19]=3)[CH:10]=2)[CH2:3][CH2:2]1)=[O:41])([CH3:38])([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 12682914-Amino-1-Boc-piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178522296N-piperidin-4-yl-3-(1H-tetrazol-5-yl)-benzamideHCID 178524335HCID 178524335, compound

Product 1

HCID 684591234-[3-(2H-tetrazol-5-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described in example 50k), N-piperidin-4-yl-3-(1H-tetrazol-5-yl)-benzamide [prepared from 3-(1H-tetrazol-5-yl)-benzoic acid by reaction with 4-amino-piperidine-carboxylic acid tert-butyl ester, N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride and N,N-dimethyl-4-aminopyridine in dichloromethane at rt in analogy to example 60d) to give 4-[3-(2H-tetrazol-5-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester followed by Boc cleavage in analogy to example 50i)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 469.4 (MH+).

Sources & evidence

ORD record
ord-53b01ed7fbc34ec5a79cd621dd30308f
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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