Hydrochloric Acid → HCID 66830378, compound

HRID 1040952Notes

Reaction equation

HRID 1040952 reaction equation
[CH2:1]([N:4]1[C:10]2[C:11]([NH2:15])=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:16])[NH:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].Cl[C:18]1[N:23]=[C:22]([NH:24][C:25]2[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=2[C:27]([NH:29][CH3:30])=[O:28])[C:21]([Cl:35])=[CH:20][N:19]=1.Cl>C(O)(C)C.O1CCOCC1.C(Cl)Cl>[CH2:1]([N:4]1[C:10]2[C:11]([NH:15][C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=4[C:27]([NH:29][CH3:30])=[O:28])[C:21]([Cl:35])=[CH:20][N:19]=3)=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:16])[NH:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideHCID 67264287HCID 67264287, compound

Product 1

HCID 66830378HCID 66830378, compoundYield 4.7%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

1-Allyl-9-amino-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (#) (68 mg, 0.31 mmol) and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide (#) (102 mg, 0.34 mmol) were combined in isopropanol (1 mL). 4 N HCl in dioxane (85 μL) was added, and the resulting mixture was heated to 120° C. in the microwave for 50 min. The resulting solution was diluted with CH2Cl2, washed with NaHCO3, dried over MgSO4, filtered, and concentrated. The resulting residue was purified with silica gel chromatography (0-100% EtOAc in hexanes) to obtain 2-[2-(1-Allyl-5-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-9-ylamino)-5-chloro-pyrimidin-4-ylamino]-N-methyl-benzamide as a white solid (7 mg, 3%). mp 186° C. (dec); LCMS: m/z=478.28 (M+H+), 1H NMR (400 MHz, CDCl3) δ 8.32 (m, 1H), 8.02 (s, 1H), 7.73 (m, 1H), 7.53 (m, 1H), 7.44 (m, 1H), 7.31 (m, 1H), 7.18 (m, 1H), 7.02 (m, 1H), 6.88 (m, 1H), 5.86 (m, 1H), 5.24 (m, 2H), 4.20 (m, 2H), 3.41 (m, 6H), 2.96 (d, J=4.5 Hz, 3H).

Workup

  1. washwashed with NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified with silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-949c890305ae4ff3b8af9f8b88b2082d
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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