Diisopropylethylamine → tert-butyl 5-((1H-pyrrole-3-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate

HRID 928383Notes

Reaction equation

HRID 928383 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.[NH2:9][CH2:10][C:11]1[C:12]([CH3:26])=[CH:13][C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:15][C:16]=1[CH3:17].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:9][CH2:10][C:11]2[C:12]([CH3:26])=[CH:13][C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[N:15][C:16]=2[CH3:17])=[O:8])=[CH:2]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 101030Pyrrole-3-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22475372N-[5-(aminomethyl)-4,6-dimethyl(2-pyridyl)] (tert-butoxy)carboxamide

Product 1

HCID 58081282tert-butyl 5-((1H-pyrrole-3-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1H-pyrrole-3-carboxylic acid (1.40 g, 12.60 mmol), tert-butyl 5-(aminomethyl)-4,6-dimethylpyridin-2-ylcarbamate (3.48 g, 13.86 mmol) and DIPEA (6.60 ml, 37.8 mmol) in DCM (100 ml) was added HBTU (5.73 g, 15.12 mmol) at rt and was stirred at rt for 12 hours. The suspension was filtered off. The solid was washed with DCM and dried under reduced pressure to afford pure tert-butyl 5-((1H-pyrrole-3-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate. HPLC (Method G) Rt=1.35 min; MS [M+H]+=345.2.

Workup

  1. filtrationThe suspension was filtered off
  2. washThe solid was washed with DCM
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-0360d1c81acd4034b2ea1222bc6ade9f
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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