Diisopropylethylamine → 4-amino-N-[(3R)-1-ethylpyrrolidin-3-yl]-3-methoxy-benzamide

HRID 2234504Notes

Reaction equation

HRID 2234504 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].[CH2:13]([N:15]1[CH2:19][CH2:18][C@@H:17]([NH2:20])[CH2:16]1)[CH3:14].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:20][C@@H:17]2[CH2:18][CH2:19][N:15]([CH2:13][CH3:14])[CH2:16]2)=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2880572486-69-3HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 51663642(3R)-1-ethylpyrrolidin-3-amine2×

Product 1

HCID 686854984-amino-N-[(3R)-1-ethylpyrrolidin-3-yl]-3-methoxy-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-amino-3-methoxybenzoic acid (Aldrich; 424 mg, 2.54 mmol) and (3R)-1-ethylpyrrolidin-3-amine (Intermediate 246; 312 mg, 2.73 mmol) in DMF (10 mL) was added DIPEA (1.4 ml, 8.04 mmol). The resultant solution was treated with HATU (1.21 g, 3.18 mmol) and stirred, under nitrogen, at ambient temperature overnight.

Sources & evidence

ORD record
ord-637585bed9cf47c88c084a6732adfd7e
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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