5-Amino-2-chloropyridine → HCID 86602138, compound

HRID 1726295Notes

Reaction equation

HRID 1726295 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.C([N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)(OC(C)(C)C)=O.Br[CH2:24][C:25]1[CH:29]=[CH:28][S:27][CH:26]=1>>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([N:1]([CH:19]2[CH2:18][CH2:17][NH:16][CH2:21][CH2:20]2)[CH2:24][C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 793055-Amino-2-chloropyridineHCID 5207033-(Bromomethyl)thiopheneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 86602138HCID 86602138, compound

Procedure

Using general procedure A with 5-amino-2-chloropyridine (254 mg, 1.98 mmol) and 1-Boc-4-piperidone (590 mg, 2.96 mmol), then general procedure H with the resulting amine and 3-(bromomethyl)thiophene (517 mg) and then using general procedure C gave (6-chloro-pyridin-3-yl)-piperidin-4-yl-thiophen-3-ylmethyl-amine as a green oil (65 mg, 10% over 3 steps).

Sources & evidence

ORD record
ord-9f961a402ac94ad8b86a7d6efe7aac97
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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