Hydrochloric Acid → HCID 66829882, compound

HRID 1687199Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=2[C:24]([NH2:26])=[O:25])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[C:18](=[O:19])[NH:17][CH2:16][CH2:15][NH:14][C:13]=3[CH:20]=2)=[N:6][CH:7]=1.Cl[C:32]1N=C(NC2C=CC=CC=2C(NC)=O)C(Cl)=CN=1.NC1C=CC2C(=O)NCCNC=2C=1.Cl.O.O1CCOCC1>COCCO.C(N(CC)CC)C>[Cl:1][C:2]1[C:3]([NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=2[C:24]([NH:26][CH3:32])=[O:25])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[C:18](=[O:19])[NH:17][CH2:16][CH2:15][NH:14][C:13]=3[CH:20]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

411 f) 2-[5-Chloro-2-(5-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]benzamide (CEP-19626). A solution of 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methylbenzamide (58 mg, 0.20 mmol) and 8-amino-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (35 mg, 0.20 mmol) in 2-methoxyethanol (5 mL) was treated with 4N HCl in 50% H2O/dioxane (50 μL, 1 equiv.) and the mixture was stirred and heated to 110° C. After 22 hrs. the mixture was cooled to room temperature, neutralized with triethylamine and concentrated. Flash chromatography (silica gel, 20% MeOH/DCM) gave 35 mg of the title compound as a pale amber solid; m.p. 232-237° C.; MS: m/z=438/440 (M+H)+, Cl-isotope pattern; 1H-NMR (DMSO-d6, δ): 11.69 (s, 1H), 9.43 (s, 1H), 8.84 (d, 8 Hz, 1H), 8.76 (s, 1H), 8.22 (s, 1H), 7.76 (d, 7 Hz, 2H), 7.67 (d, 8 Hz, 1H), 7.48 (m, 2H), 7.15 (t, 8 Hz, 1H), 7.03 (s, 1H), 6.90 (d, 9 Hz, 1H), 3.10 (m, 2H), 2.82 (s, 3H), 2.60 (m, 2H).

Workup

temperaturethe mixture was cooled to room temperature
concentrationconcentrated

Sources & evidence

ORD record: ord-f059d30b5b684a3395d0ecb7a470536d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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