4-{3-[2-Methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-ylamino]-propyl}-tetrahydro-pyran-4-carboxylic acid methyl ester → Ammonia

HRID 2401120Notes

Reaction equation

HRID 2401120 reaction equation
C[O:2][C:3]([C:5]1([CH2:11][CH2:12][CH2:13][NH:14][C:15]2[C:16]([CH3:32])=[N:17][C:18]([N:21]3[CH2:25][CH2:24][C@@H:23]([N:26]4[CH2:30][CH2:29][CH2:28][C@@H:27]4[CH3:31])[CH2:22]3)=[CH:19][CH:20]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=O>CO.C(Cl)Cl>[CH3:32][C:16]1[C:15]([N:14]2[CH2:13][CH2:12][CH2:11][C:5]3([CH2:6][CH2:7][O:8][CH2:9][CH2:10]3)[C:3]2=[O:2])=[CH:20][CH:19]=[C:18]([N:21]2[CH2:25][CH2:24][C@@H:23]([N:26]3[CH2:30][CH2:29][CH2:28][C@@H:27]3[CH3:31])[CH2:22]2)[N:17]=1.[NH3:14]

Participants

4

Reactant 1

HCID 712804014-{3-[2-Methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-ylamino]-propyl}-tetrahydro-pyran-4-carboxylic acid methyl ester

Product 2

HCID 222AmmoniaYield 5%HCID 54590986HCID 54590986, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound is synthesized in essentially the same manner using the procedures as set forth in Step 2 of Example 1, by cyclizing 4-{3-[2-methyl-6-((2S,3′R)-2-methyl-[1,3′]bipyrrolidinyl-1′-yl)-pyridin-3-ylamino]-propyl}-tetrahydro-pyran-4-carboxylic acid methyl ester (44 mg, 0.10 mmol) to obtain 13.5 mg (33% yield over two steps) of the title compound after flash column chromatography (5% 7N NH3 in MeOH/CH2Cl2).

Workup

  1. customThe title compound is synthesized in essentially the same manner

Sources & evidence

ORD record
ord-26fce3e734a844ddab70c87fe6f911b6
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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