Tert-Butylamine → HCID 90040556, compound

HRID 523028Notes

Reaction equation

HRID 523028 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:11]([C:12]([OH:14])=O)=[CH:10][N:9]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]2=[N:6][C:7]=1[Cl:8].Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1.[CH3:45][C:46]([NH2:49])([CH3:48])[CH3:47]>CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[C:4]2[C:11]([C:12]([NH:49][C:46]([CH3:48])([CH3:47])[CH3:45])=[O:14])=[CH:10][N:9]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]2=[N:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 6385Tert-ButylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 90040555HCID 90040555, compound

Product 1

HCID 90040556HCID 90040556, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-3-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (600 mg, 1.48 mmol) in DMF (5 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (650 mg, 3.39 mmol) and HOBT (520 mg, 3.39 mmol) and the mixture stirred for 10 min. 2-methylpropan-2-amine (432 mg, 5.9 mmol) was added and the mixture stirred at room temperature for 16 h, then diluted with 10% citric acid and ethyl acetate. The organic layer was separated and washed with 10% citric acid, saturated aqueous NaHCO3 and brine, then concentrated in vacuo and purified by chromatography (silica, 5-20% ethyl acetate in hexanes) to give 2-bromo-N-tert-butyl-3-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (530 mg, 1.15 mmol, 78%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.30 (s, 1H), 7.72 (s, 1H), 5.64 (s, 2H), 3.57 (t, J=8.3 Hz, 2H), 1.56 (s, 9H), 0.96 (t, J=8.3 Hz, 2H), 0.01 (s, 9H).

Workup

  1. stirringthe mixture stirred at room temperature for 16 h
  2. customThe organic layer was separated
  3. washwashed with 10% citric acid, saturated aqueous NaHCO3 and brine
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography (silica, 5-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-709a9e88789b4c98bcf92aac6a94fbfd
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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