Triethylamine → (S)-tert-butyl (1-((3-(2-((4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxamido)propyl)amino)-1-oxopropan-2-yl)(methyl)carbamate

HRID 2284693Notes

Reaction equation

HRID 2284693 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([C:11]([NH2:13])=[O:12])=[CH:9][N:8]=[CH:7][N:6]=1)[CH2:2][CH3:3].[C:14]([N:21]([CH3:27])[C@H:22]([C:24]([OH:26])=O)[CH3:23])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].Cl.C(N=C=N[CH2:34][CH2:35][CH2:36][N:37](C)C)C.[OH2:40].O[N:42]1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2N=N1.C([N:53]([CH2:56]C)CC)C>C(OCC)(=O)C.O.CN(C)C=O>[C:56]([C:49]1[CH:50]=[CH:45][C:46]([NH:42][C:7]2[N:6]=[C:5]([NH:4][CH2:1][CH2:2][CH3:3])[C:10]([C:11]([NH:13][CH2:34][CH2:35][CH2:36][NH:37][C:24](=[O:26])[C@@H:22]([N:21]([CH3:27])[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH3:23])=[O:12])=[CH:9][N:8]=2)=[CH:47][CH:48]=1)(=[O:40])[NH2:53]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 1317335334-(Propylamino)pyrimidine-5-carboxamide

Product 1

HCID 90051734(S)-tert-butyl (1-((3-(2-((4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxamido)propyl)amino)-1-oxopropan-2-yl)(methyl)carbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To N-(3-aminopropyl)-2-(4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxamide (D3) trifluoroacetate (100 mg), N-Boc-N-methyl-L-alanine (47 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (128 mg) and 1-hydroxybenzotriazole monohydrate (102 mg), N,N-dimethylformamide (2 mL) and triethylamine (116 μL) were added at room temperature, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain (S)-tert-butyl (1-((3-(2-((4-carbamoylphenyl)amino)-4-(propylamino)pyrimidine-5-carboxamido)propyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (D4, 103 mg) as white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-774f08d1cddf42fabe9d7e5bd8620ac8
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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