Hydrogen Bromide → 3-Amino-5-(4-methoxyphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one

HRID 593485Notes

Reaction equation

HRID 593485 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[CH:31]=[CH:30][CH:29]=[CH:28][C:11]=3[NH:12][C:13](=[O:27])[CH:14]([NH:16]C(=O)OCC3C=CC=CC=3)[N:15]=2)=[CH:5][CH:4]=1.Br.CCOCC>C(O)(=O)C>[NH2:16][CH:14]1[C:13](=[O:27])[NH:12][C:11]2[CH:28]=[CH:29][CH:30]=[CH:31][C:10]=2[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:15]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 68186038HCID 68186038, compound

Product 1

HCID 219556023-Amino-5-(4-methoxyphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-oneYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Intermediate 6B (1000 mg, 2.407 mmol) was treated with 33% HBr in acetic acid (5 mL) to give a suspension. The reaction mixture was then heated to 70° C. for 3 hrs with stirring. The reaction mixture was then poured into ether (100 mL). The resulting solid was filtered and then partitioned between DCM (100 mL)/saturated NaHCO3 (100 mL). The aqueous phase was back extracted with DCM (3×100 mL). The combined organic phases were dried with MgSO4, filtered and concentrated to provided Intermediate 6C (0.608 g, 90%). 1H NMR (400 MHz, DMSO-d6) δ 10.61 (br. s., 1H), 7.62-7.53 (m, 1H), 7.44 (d, J=8.8 Hz, 2H), 7.34-7.23 (m, 2H), 7.23-7.17 (m, 1H), 6.99 (d, J=9.0 Hz, 2H), 4.20 (s, 1H), 3.81 (s, 3H).

Workup

  1. customto give a suspension
  2. filtrationThe resulting solid was filtered
  3. custompartitioned between DCM (100 mL)/saturated NaHCO3 (100 mL)
  4. extractionThe aqueous phase was back extracted with DCM (3×100 mL)
  5. dry with materialThe combined organic phases were dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-337b85968fe24b35b69a6b37eb9aba1b
Source dataset
uspto-grants-2016_01
Patent number
US09242940B2

Reaction notes

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