Dichloromethane methanol → HCID 66829890, compound

HRID 1040892Notes

Reaction equation

HRID 1040892 reaction equation
[Cl:1][C:2]1[C:3]([NH:23][C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([NH:28][CH3:29])=[O:27])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[C:18](=[O:19])[N:17]([CH3:20])[CH2:16][CH2:15][N:14]([CH3:21])[C:13]=3[CH:22]=2)=[N:6][CH:7]=1.CO.C(Cl)[Cl:37]>>[NH2:8][C:9]1[CH:10]=[CH:11][C:12]2[C:18](=[O:19])[N:17]([CH3:20])[CH2:16][CH2:15][N:14]([CH3:21])[C:13]=2[CH:22]=1.[Cl:37][C:5]1[N:4]=[C:3]([NH:23][C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([NH:28][CH3:29])=[O:27])[C:2]([Cl:1])=[CH:7][N:6]=1.[Cl:1][C:2]1[C:3]([NH:23][C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([NH:28][CH3:29])=[O:27])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[C:18](=[O:19])[N:17]([CH3:20])[CH2:16][CH2:15][N:14]([CH3:21])[C:13]=3[CH:22]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 66829890HCID 66829890, compound

Product 3

HCID 57853850HCID 57853850, compoundHCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideHCID 66829890HCID 66829890, compoundYield 43%

Procedure

Part 3C. 2-[5-Chloro-2-(1,4-dimethyl-5-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-N-methylbenzamide. This compound was prepared according to Example 411f. From 8-amino-1,4-dimethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (100 mg, 0.49 mmol) and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methylbenzamide (144 mg, 0.49 mmol) was obtained 97 mg (43%) of the title compound following flash chromatography (silica gel, 20% MeOH/DCM); m.p. 243-247° C.; MS: m/z=466/468 (M+H)+, Cl-isotope pattern; 1H-NMR (DMSO-d6, δ): 11.64 (s, 1H), 9.57 (s, 1H), 8.76 (m, 2H), 8.27 (s, 1H), 7.76 (d, 8 Hz, 1H), 7.50 (t, 7 Hz, 1H), 7.40 (d, 7 Hz, 1H), 7.33 (d, 8 Hz, 1H), 7.20 (s, 1H), 7.15 (t, 7 Hz, 1H), 3.42 (t, 5 Hz, 2H), 3.25 (t, 5 Hz, 2H), 3.04 (s, 3H), 2.81 (s, 3H), 2.68 (s, 3H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-fd645c2c484746dfb0598404dfd9ad0a
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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