Dimethylamine → 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxamide

HRID 41227Notes

Reaction equation

HRID 41227 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13]2[CH:14]=[C:15]([C:31]([OH:33])=O)[CH:16]=[C:17]3[C:22]=2[O:21][C:20]([N:23]2[CH2:28][CH2:27][O:26][C@H:25]([CH3:29])[CH2:24]2)=[CH:19][C:18]3=[O:30])[CH:5]=[CH:6][CH:7]=1.[CH3:34][NH:35][CH3:36]>>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13]2[CH:14]=[C:15]([C:31]([N:35]([CH3:36])[CH3:34])=[O:33])[CH:16]=[C:17]3[C:22]=2[O:21][C:20]([N:23]2[CH2:28][CH2:27][O:26][C@H:25]([CH3:29])[CH2:24]2)=[CH:19][C:18]3=[O:30])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 866724438-(1-(3-fluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acid

Product 1

HCID 665582318-(1-(3-fluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxamideYield 47%

Procedure

8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acid (102 mg, 0.23 mmol) was reacted with dimethylamine (2N in THF) (0.169 ml, 0.34 mmol) as described in Example 3.02 to give 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxamide (51 mg, 47%) as a pale yellow foam.

Sources & evidence

ORD record
ord-4519fb3b64fe4f42b07decf43d0bb91b
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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