Ammonia → HCID 89783332, compound

HRID 1056293Notes

Reaction equation

HRID 1056293 reaction equation
[C:1]([NH:5][C:6]1[C:7]([CH3:27])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:20][C:19]([CH:21]3[CH2:23][CH2:22]3)=[C:18]([C:24]([OH:26])=O)[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].CC[N:30](C(C)C)C(C)C.N.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[C:1]([NH:5][C:6]1[C:7]([CH3:27])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:20][C:19]([CH:21]3[CH2:22][CH2:23]3)=[C:18]([C:24]([NH2:30])=[O:26])[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89783677HCID 89783677, compound

Product 1

HCID 89783332HCID 89783332, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-2-cyclopropyl-1H-pyrrole-3-carboxylic acid (418c) (0.15 g, 0.412 mmol), 0-(-7-azabenzotriazol-1-yl)-n,′n,′n,′n′-tetramethyluronium-hexafluorophosphate (GenScript Corporation, 0.196 g, 0.514 mmol), DIPEA (Sigma Aldrich, 0.179 ml, 1.029 mmol), in DMF (2.058 mL) was stirred at RT for 5 min before addition of ammonia (2.0 M solution in MeOH, 0.412 mL, 0.823 mmol). Reaction mixture was stirred at RT overnight. Additional aliquots of HATU and DIPEA were added to the reaction mixture which was stirred at RT overnight. Reaction mixture was diluted with DCM and washed with water and brine to remove DMF. Purification by Biotage (0-10% MeOH/DCM) produced 5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-2-cyclopropyl-1H-pyrrole-3-carboxamide (418) (0.028 g, 0.078 mmol, 19% yield). 1H NMR (300 MHz, MeOH-d4) δ ppm 0.82-0.92 (m, 2H) 0.98-1.08 (m, 2H) 1.65 (s, 9H) 2.30-2.45 (m, 1H) 2.57 (s, 3H) 6.93-6.99 (m, 1H) 7.26-7.39 (m, 1H) 7.56-7.65 (m, 1H) 7.75-7.85 (m, 1H). m/z (ESI, +ve) 364.1 (M+H).

Workup

  1. customReaction mixture
  2. stirringwas stirred at RT overnight
  3. customReaction mixture
  4. washwashed with water and brine
  5. customto remove DMF
  6. customPurification by Biotage (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-354c58e64a804727bb5ee1e0fb2df460
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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