4-Methylmorpholine → HCID 178455634, compound

HRID 447929Notes

Reaction equation

HRID 447929 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]([NH:12][CH2:13][C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=2[O:22][CH3:23])=[NH:11])[S:7][CH:8]=1.[CH2:24]([S:28](Cl)(=[O:30])=[O:29])[CH2:25][CH2:26][CH3:27].CN1CCOCC1>C1COCC1>[CH3:21][O:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([O:22][CH3:23])[C:14]=1[CH2:13][NH:12][C:10]([NH:9][C:6]1[S:7][CH:8]=[C:4]([CH2:3][NH:2][S:28]([CH2:24][CH2:25][CH2:26][CH3:27])(=[O:30])=[O:29])[N:5]=1)=[NH:11]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 754301-Butanesulfonyl chlorideHCID 178491368HCID 178491368, compound

Product 1

HCID 178455634HCID 178455634, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 100 mg (0.33 mmol) N-[4-(aminomethyl)-1,3-thiazole-2-yl]-N′-(2,6-dimethoxybenzyl)guanidine hydrochloride, Example 154 free base, with 60.4 mg butane sulfonic acid chloride in 5 ml THF with addition of 480 mg polymer-bound NMM (1.7 mmol/g; Argonaut) and chromatography of the crude product on silica gel dichloromethane/methanol 0-2%) yielded 46 mg; ESI-MS [M+H+]=442.05.

Workup

  1. customyielded 46 mg

Sources & evidence

ORD record
ord-ca54ba8278834fcd9b7ecd12b9cb15fb
Source dataset
uspto-grants-2013_07
Patent number
US08481576B2

Reaction notes

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