Methyl 6-aminonicotinate → HCID 67354499, compound

HRID 1850595Notes

Reaction equation

HRID 1850595 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]([C:5]1[N:14]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]2[N:9]=[C:10](Cl)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[CH3:22][O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[N:27][CH:26]=1>>[CH3:22][O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:10]2[N:11]=[CH:12][C:7]3[CH:6]=[C:5]([C:3](=[O:4])[N:2]([CH3:21])[CH3:1])[N:14]([CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)[C:8]=3[N:9]=2)=[N:27][CH:26]=1

Participants

3

Reactant 2

HCID 737487Methyl 6-aminonicotinateHCID 86686647HCID 86686647, compound

Product 1

HCID 67354499HCID 67354499, compoundYield 65.1%

Procedure

Following general N—C coupling procedure 1, 2-chloro-7-cyclohexyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (800 mg, 2.61 mmol), was combined with 6-amino-nicotinic acid methyl ester (397 mg, 2.61 mmol) which gave 6-(7-cyclohexyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-nicotinic acid methyl ester (720 mg, 1.70 mmol) in 65% yield. MS m/z 423.6 (M+H)+.

Sources & evidence

ORD record
ord-9beaf539d2d7417cb28633af33c90676
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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