3-Fluorophenyl isocyanate → HCID 18696521, compound

HRID 1870655Notes

Reaction equation

HRID 1870655 reaction equation
[NH2:1][CH:2]1[C:8]([CH3:10])([CH3:9])[S:7][C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[N:4]([CH2:15][C:16]([N:18]([CH:27]([CH3:29])[CH3:28])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:17])[C:3]1=[O:30].[F:31][C:32]1[CH:33]=[C:34]([N:38]=[C:39]=[O:40])[CH:35]=[CH:36][CH:37]=1>C(Cl)Cl>[F:31][C:32]1[CH:33]=[C:34]([NH:38][C:39](=[O:40])[NH:1][CH:2]2[C:8]([CH3:9])([CH3:10])[S:7][C:6]3[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=3[N:4]([CH2:15][C:16]([N:18]([CH:27]([CH3:28])[CH3:29])[C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)=[O:17])[C:3]2=[O:30])[CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 1230643-Fluorophenyl isocyanateHCID 54549705HCID 54549705, compound

Product 1

HCID 18696521HCID 18696521, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Similarly to Example 22, to 2-(3-amino-2,2-dimethyl-4-oxo-3,4-dihydro-2H-benzo [b][1,4]thiazepin-5-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide, intermediate 34 G (300 mg, 0.70 mmol) in DCM (2 mL) was added m-fluorophenyl isocyanate (0.80 mL, 0.70 mmol) to give the crude titled compound (225 mg, 57%). A sample (75 mg) was purifid by RP-HPLC (40-60%, over 30 min) to give the titled product (47 mg). tR =20.9 min (40-60%, over 30 min); 1HNMR (300 MHz, d6-DMSO) d 0.96 (d, J=6.2 Hz, 3H), 1.21 (s, 6H), 3.59 (d, J=16.2 Hz, 1H), 3.76 (s, 3H), 4.26 (d, J=7.8, 1H), 4.55 (d, J=16.2, 1H), 4.80 (m, 1H), 6.74 (m, 1H), 7.19 (m, 3H), 7.20 (m, 2H), 7.32 (m, 1H), 7.49 (m, 1H), 7.60 (m, 2H), 9.03 (s, 1H); MS(FAB) m/z 565.1 (MH+).

Workup

  1. customto give the crude titled compound (225 mg, 57%)
  2. customwas purifid by RP-HPLC (40-60%, over 30 min)

Sources & evidence

ORD record
ord-5d6da41cfaf7441ca81b94456c0daa0d
Source dataset
uspto-grants-2000_08
Patent number
US06096885

Reaction notes

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