Triethylamine → HCID 25182930, compound

HRID 1746759Notes

Reaction equation

HRID 1746759 reaction equation
[CH:1]1([N:7]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][C:18]=3[CH3:27])=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[C:33]([O:37][C:38](=[O:42])[CH2:39][CH2:40][NH2:41])([CH3:36])([CH3:35])[CH3:34].C(N(CC)CC)C>C1COCC1>[CH:1]1([N:7]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23]([NH:41][CH2:40][CH2:39][C:38]([O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:42])(=[O:25])=[O:24])=[CH:19][C:18]=3[CH3:27])=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 594468814-[({6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]-3-methylbenzenesulfonyl chloride2×

Product 1

HCID 25182930HCID 25182930, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[({6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]-3-methylbenzenesulfonyl chloride (Intermediate 20, 100 mg; 0.22 mmol) in anhydrous THF (10 ml) was treated with beta-alanine tert-butyl ester hydrochloride (Bachem, 43 mg; 0.24 mmol) and triethylamine (60 μl; 0.43 mmol). After stirring for 4 hours, the precipitate was filtered and purified by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc, to give the title compound as a yellow solid.

Workup

  1. filtrationthe precipitate was filtered
  2. custompurified by column chromatography (silica)
  3. washeluting with cyclohexane containing
  4. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-6ec4977bd4fa4f5d99e1ed9c946ca52d
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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