Diisopropylethylamine → methyl 4-(aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylate

HRID 1875005Notes

Reaction equation

HRID 1875005 reaction equation
[Cl:1][C:2]1[C:3]([C:11]([OH:13])=O)=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].CC[N:16](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>[NH2:16][C:11]([C:3]1[C:2]([Cl:1])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[NH:5][CH:4]=1)=[O:13]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 684862114-chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-3-carboxylic acid

Product 1

HCID 68487265methyl 4-(aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylateYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-3-carboxylic acid (0.075 g, 0.368 mmol) in DMF (1 mL) was added DIPEA (0.097 mL, 0.553 mmol) and HATU (0.168 g, 0.442 mmol). Ammonia was bubbled through the reaction mixture for 5 min. and the reaction stirred at RT for 1 h. The crude material was purified by HPLC. The desired fractions were collected and lypholized to afford methyl 4-(aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylate (0.044 g, 59% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.40-12.56 (m, 1H) 7.54 (d, 1H) 7.29 (br. s., 1H) 7.13 (br. s., 1H) 3.80 (s, 3H). MS: m/z 203.0 (M+1).

Workup

  1. customAmmonia was bubbled through the reaction mixture for 5 min.
  2. customThe crude material was purified by HPLC
  3. customThe desired fractions were collected

Sources & evidence

ORD record
ord-c3c79e1f11aa4352a09de2dcff399c4a
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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