N-BOC-ethylenediamine → Tert-butyl 2-((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methylamino)ethylcarbamate

HRID 1685076Notes

Reaction equation

HRID 1685076 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[CH2:19][NH:20][C:21]([NH:23][C:24]1[S:25][CH:26]=[C:27]([CH:29]=O)[N:28]=1)=[O:22].[NH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41]>C(Cl)Cl>[F:15][C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[CH2:19][NH:20][C:21](=[O:22])[NH:23][C:24]1[S:25][CH:26]=[C:27]([CH2:29][NH:34][CH2:35][CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:41])[CH3:43])[N:28]=1

Participants

5

Reactant 3

HCID 187201N-BOC-ethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 580550461-(3-Fluorobenzyl)-3-(4-formylthiazol-2-yl)urea

Product 1

HCID 58055091Tert-butyl 2-((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methylamino)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (937 mg, 4.42 mmol) was added to a CH2Cl2 (50 mL) solution of 1-(3-fluorobenzyl)-3-(4-formylthiazol-2-yl)urea (620 mg, 2.21 mmol) and tert-butyl 2-aminoethylcarbamate (532 mg, 3.32 mmol) at 0 C. Upon completion of the reaction, it was quenched with dilute NaHCO3. The organics were dried and evaporated. Flash chromatography afforded tert-butyl 2-((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methylamino)ethylcarbamate. 1H NMR (400 MHz, CDCl3): δ 8.05 (1H, br), 7.28 (m, 1H), 7.00 (m, 3H), 6.61 (s, 1H), 4.80 (s, 1H), 4.49 (d, 2H), 3.73 (s, 2H), 3.17 (m, 2H), 2.63 (t, 2H), 1.41 (s, 9H). MS (ES+): M/Z 424 (M+H)+.

Workup

  1. customUpon completion of the reaction, it
  2. customwas quenched with dilute NaHCO3
  3. customThe organics were dried
  4. customevaporated

Sources & evidence

ORD record
ord-47f93205b0cf4d498cb335a0671610b2
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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