Hydrochloric Acid → HCID 25157619, compound

HRID 1040690Notes

Reaction equation

HRID 1040690 reaction equation
[NH2:1][C:2]1[C:12]2[C:11](=[O:13])[NH:10][CH2:9][CH2:8][N:7](C(=O)C(F)(F)F)[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34]([NH:37][CH3:38])(=[O:36])=[O:35])[C:24]([Cl:39])=[CH:23][N:22]=1.Cl>C(O)(C)C.O1CCOCC1>[Cl:39][C:24]1[C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34]([NH:37][CH3:38])(=[O:36])=[O:35])=[N:26][C:21]([NH:1][C:2]2[C:12]3[C:11](=[O:13])[NH:10][CH2:9][CH2:8][NH:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)=[N:22][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 58748359HCID 58748359, compoundHCID 86633855HCID 86633855, compound

Product 1

HCID 25157619HCID 25157619, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneCatalystHCID 3776IsopropanolSolvent

Procedure

Into a microwave vial was placed 6-amino-1-(2,2,2-trifluoro-acetyl)-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (25 mg, 0.092 mmol) and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzenesulfonamide (27 mg, 0.082 mmol) in isopropyl alcohol (3 mL) with 4 M HCl in dioxane (˜2 drops). The mixture was subjected to microwaves at 120° C. for 10 minutes. Trace starting materials were present so the reaction mixture was resubjected to the same microwave conditions. The resulting solid was collected by filtration and washed with cold methylene chloride and dried in a vacuum oven at 50° C. overnight to give product as an off-white solid 2-[5-Chloro-2-(5-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-6-ylamino)pyrimidin-4-ylamino]-N-methylbenzene-sulfonamide (6 mg, 16% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.60 (s, 1H), 9.62 (s, 1H), 9.04 (d, 1H, J=8 Hz), 8.95-8.86 (m, 3H), 8.55 (s, 1H), 7.88-7.25 (m, 4H), 6.71 (d, 1H, J=7.8 Hz), 6.52 (s, 1H), 3.46 (m, 2H), 2.84 (d, 3H), 2.5 (m, 2H); MS (m/e) 474 (M+1)

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with cold methylene chloride
  3. customdried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-9ade93a516e847588148fc85187b0631
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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