Triethylamine → HCID 57883815, compound

HRID 253865Notes

Reaction equation

HRID 253865 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:25]2[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]2)[C:15]([NH:17][C:18]2[S:19][C:20]([CH:23]=O)=[CH:21][N:22]=2)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.N1([CH2:39][CH2:40][S:41]([NH2:44])(=[O:43])=[O:42])CCNCC1.C([N:47]([CH2:50][CH3:51])[CH2:48][CH3:49])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH:25]2[CH2:26][CH2:27][CH:28]([CH3:31])[CH2:29][CH2:30]2)[C:15]([NH:17][C:18]2[S:19][C:20]([CH2:23][N:47]3[CH2:48][CH2:49][N:44]([S:41]([CH2:40][CH3:39])(=[O:43])=[O:42])[CH2:51][CH2:50]3)=[CH:21][N:22]=2)=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 578838034-[3-(5-Formyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl esterHCID 86611202Piperazine ethane sulfonamide hydrochloride

Product 1

HCID 57883815HCID 57883815, compoundYield 58%

Procedure

Prepared as described in general procedure (P) using 4-[3-(5-formyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 0.45 mmol), piperazine ethane sulfonamide hydrochloride (125 mg, 0.58 mmol), triethyl amine (80 μL, 0.58 mmol) and sodium triacetoxyborohydride (113 mg, 0.53 mmol) to afford 160 mg (58%) of the desired product after purification.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1136de6489a044c98272bb64c11b9a47
Source dataset
uspto-grants-2011_01
Patent number
US07872139B2

Reaction notes

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