Ethyl Acetate → tert-Butyl 2-(6-chloronicotinamido)-4-(thiophen-2-yl)phenylcarbamate

HRID 1173151Notes

Reaction equation

HRID 1173151 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][C:9]=1[NH2:19])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][N:23]=1.CC[O:32]C(C)=O>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][C:9]=1[NH:19][C:26]([C:25]1[CH:24]=[N:23][C:22]([Cl:21])=[CH:29][CH:28]=1)=[O:32])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 57717453tert-Butyl 2-(6-chloronicotinamido)-4-(thiophen-2-yl)phenylcarbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of tert-butyl[2-amino-4-(2-thienyl)phenyl]carbamate (E) (600 mg, 2.07 mmol) and 6-chloronicotinyl chloride (380 mg, 2.16 mmol) in 5 mL of pyridine was stirred overnight, poured into EtOAc and washed with saturated NaHCO3, dried (Na2SO4) and concentrated giving the BOC-protected chloronicotinamide (F): 1H NMR (600 MHz, CD3OD): δ 8.95 (d, J=2.3 Hz, 1H), 8.35 (dd, J=8.2 Hz, 2.3 Hz, 1H), 7.85 (br s, 1H), 7.62 (d, J=8.5 Hz, 1H), 7.55-7.51 (m, 2H), 7.37-7.35 (m, 2H), 7.07 (dd, J=5.0 Hz, 3.5 Hz, 1H), 4.59 (s, 1H), 1.49 (s, 9H); MS (ESI+): cal'd [M+Na]+ 452.1, obs'd 452.1.

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ba1e77588b0a46b792d3c0c00bdc98f3
Source dataset
uspto-grants-2010_11
Patent number
US07834026B2

Reaction notes

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