Trifluoroacetic acid → 1-(azepan-4-yl)-4-methoxy-N-(1-methylcyclobutyl)piperidine-4-carboxamide TFA salt

HRID 714540Notes

Reaction equation

HRID 714540 reaction equation
[CH3:1][O:2][C:3]1([C:23](=[O:30])[NH:24][C:25]2([CH3:29])[CH2:28][CH2:27][CH2:26]2)[CH2:8][CH2:7][N:6]([CH:9]2[CH2:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32]>C(Cl)Cl>[OH:37][C:31]([C:33]([F:36])([F:35])[F:34])=[O:32].[NH:12]1[CH2:13][CH2:14][CH2:15][CH:9]([N:6]2[CH2:7][CH2:8][C:3]([O:2][CH3:1])([C:23]([NH:24][C:25]3([CH3:29])[CH2:26][CH2:27][CH2:28]3)=[O:30])[CH2:4][CH2:5]2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117678314Tert-butyl 4-{4-methoxy-4-[(1-methylcyclobutyl)carbamoyl]piperidin-1-yl}azepane-1-carboxylate

Product 1

HCID 1317340601-(azepan-4-yl)-4-methoxy-N-(1-methylcyclobutyl)piperidine-4-carboxamide TFA salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 4-{4-methoxy-4-[(1-methylcyclobutyl)carbamoyl]piperidin-1-yl}azepane-1-carboxylate (0.25 g, 0.06 mmol) was dissolved in DCM (4 mL) and TFA (1 mL) was added. The reaction mixture was stirred at rt overnight under nitrogen, then the solvents were removed in vacuo, to give 1-(azepan-4-yl)-4-methoxy-N-(1-methylcyclobutyl)piperidine-4-carboxamide TFA salt (0.26 g), Intermediate 7, as a dark yellow oil which was used directly without further purification.

Workup

  1. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-5865e5664d6d404e8dc059568b04f369
Source dataset
uspto-grants-2015_11
Patent number
US09187451B2

Reaction notes

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