Triethylamine → HCID 57883815, compound

HRID 1818356Notes

Reaction equation

HRID 1818356 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-30bc9b2a19a94ce6a4b601295c35a5f9
Source dataset
uspto-grants-2009_10
Patent number
US07598391B2

Reaction notes

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