4-Chlorophenyl Isocyanate → HCID 69593688, compound

HRID 1244544Notes

Reaction equation

HRID 1244544 reaction equation
Cl.[CH3:2][N:3]([CH3:24])[C:4]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C@H:19]2[CH2:23][CH2:22][CH2:21][NH:20]2)=[O:18])=[CH:12][CH:11]=1)=[N:5][S:6]([CH3:9])(=[O:8])=[O:7].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1>C(Cl)Cl>[CH3:2][N:3]([CH3:24])[C:4]([C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]([C@H:19]2[CH2:23][CH2:22][CH2:21][N:20]2[C:33]([NH:32][C:29]2[CH:30]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=2)=[O:34])=[O:18])=[CH:14][CH:15]=1)=[N:5][S:6]([CH3:9])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 69104510HCID 69104510, compound

Product 1

HCID 69593688HCID 69593688, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part F: 10.6 mg (0.028 mmol) of the hydrochloride were dissolved in 2 mL of anhydrous CH2Cl2. 2 eq of TEA and 1 eq of p-chlorophenyl isocyanate were added, and the mixture was stirred under N2 atmosphere for 8 h. Volatiles were evaporated. 3 mL of CH2Cl2 were added and the mixture was washed twice with 1 mL of water, dried over MgSO4, and concentrated. The crude product was purified by prep HPLC to give the title compound. 1H NMR (500 MHz, CDCl3) δ 9.76 (s, 1H), 7.45–7.24 (m, 8H), 6.4 (s, 1H), 4.72 (d, J=5 Hz, 1H), 3.6 (m, 1H), 3.45 (m, 1H), 3.25 (s, 3H) 2.93 (s, 3H), 2.84 (s, 3H), 2.65 (m, 1H), 2.3–1.9 (m, 3H), ppm. LC-MS (ESI) 492.15 [M+H]+, tR=4.928 min (Shimadzu Phenomenex S5 ODS 4.6×50 mm Luna flow rate 2.5 ml/mn; detection at 220 nM; Gradient elution 0% to 100% B over 8 min; (A=10% MeOH, 90% H2O, 0.2% H3PO4 & B=90% MeOH, 10% H2O, 0.2% H3PO4). HRMS (ESI) m/z calcd for C22H27N5O4SCl [M+H]+ 492.14724, found 492.1506.

Workup

  1. customVolatiles were evaporated
  2. addition3 mL of CH2Cl2 were added
  3. washthe mixture was washed twice with 1 mL of water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-530ae93fa8f54006a1c02972985d6a4c
Source dataset
uspto-grants-2006_10
Patent number
US07122557B2

Reaction notes

Loading…