Acetonitrile → HCID 67283319, compound

HRID 1910711Notes

Reaction equation

HRID 1910711 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:10]=3[N:11](CC3C=CC(OC)=CC=3)[C:12](=[O:23])[CH:13]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[N:14]=2)=[CH:4][N:3]=1.C(#N)C>O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:9]3[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:10]=3[NH:11][C:12](=[O:23])[CH:13]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[N:14]=2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 67282345HCID 67282345, compound

Product 1

HCID 67283319HCID 67283319, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ceric ammonium nitrate (201 mg, 2.6 eq) was added portionwise to a stirred solution of 5-(2-aminopyrimidin-5-yl)-7-chloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (75 mg) in 9:1 acetonitrile:water (9 mL:1 mL). The reaction was stirred at room temperature overnight, and then another 200 mg of ceric ammonium nitrate was added. The reaction was stirred another 3 h, and then concentrated in vacuo. The crude was partitioned between EtOH and saturated potassium carbonate. The aqueous layer was re-extracted with ethanol 4×. The combined extracts were then dried over sodium sulfate, then concentrated and purified by chromatography (Gradient: 3:1 hexanes:EtOAc to EtOAc) yielding product (44 mg, 76% yield). 1HNMR (300 MHz, DMSO-d6) δ10.78 (s, 1H), 8.18 (s, 2H), 7.62 (d, 1H), 7.50-7.13 (m, 8H), 3.70 (m, 1H), 3.50-3.32 (m, 2H). HRMS (ES+) m/z calcd for C20H15Cl2N5O [M+H]+, 412.0732. found, 412.0726.

Workup

  1. stirringThe reaction was stirred another 3 h
  2. concentrationconcentrated in vacuo
  3. customThe crude was partitioned between EtOH and saturated potassium carbonate
  4. extractionThe aqueous layer was re-extracted with ethanol 4×
  5. dry with materialThe combined extracts were then dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by chromatography (Gradient: 3:1 hexanes:EtOAc to EtOAc)

Sources & evidence

ORD record
ord-6ae19ce47c1e40e1aef152a47955452b
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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