1-Boc-3-aminopyrrolidine → HCID 60207420, compound

HRID 1192201Notes

Reaction equation

HRID 1192201 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].[NH2:21][CH:22]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23]1>>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:21][CH:22]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23]2)=[O:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 27563701-Boc-3-aminopyrrolidineHCID 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acid

Product 1

HCID 60207420HCID 60207420, compound

Procedure

Prepared according to the procedure described for example 70 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylic acid (3.0 g, 8.5 mmol) 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (3.5 g, 9.3 mmol) and tert-butyl 3-aminopyrrolidine-1-carboxylate (1.86 g, 0.52 mmol). The title compound was obtained as a solid (3.1 g, 70% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.98 (2H, s), 8.91 (1H, m), 8.52 (1H, s), 4.29 (1H, m), 3.49 (1H, m), 3.30 (1H, m), 3.15 (1H, m), 2.06 (1H, m), 2.03 (1H, m), 1.83 (1H, m), 1.40 (9H, s).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-724d60ec6880435b8c6443f96c91f6e0
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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