Dichloromethane methanol → HCID 66830431, compound

HRID 1040893Notes

Reaction equation

HRID 1040893 reaction equation
[Cl:1][C:2]1[C:3]([NH:22][C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([NH:27][CH3:28])=[O:26])=[N:4][C:5]([NH:8][C:9]2[CH:21]=[CH:20][C:12]3[N:13]([CH3:19])[CH2:14][CH2:15][NH:16][C:17](=[O:18])[C:11]=3[CH:10]=2)=[N:6][CH:7]=1.CO.C(Cl)[Cl:36]>>[NH2:8][C:9]1[CH:21]=[CH:20][C:12]2[N:13]([CH3:19])[CH2:14][CH2:15][NH:16][C:17](=[O:18])[C:11]=2[CH:10]=1.[Cl:36][C:5]1[N:4]=[C:3]([NH:22][C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([NH:27][CH3:28])=[O:26])[C:2]([Cl:1])=[CH:7][N:6]=1.[Cl:1][C:2]1[C:3]([NH:22][C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([NH:27][CH3:28])=[O:26])=[N:4][C:5]([NH:8][C:9]2[CH:21]=[CH:20][C:12]3[N:13]([CH3:19])[CH2:14][CH2:15][NH:16][C:17](=[O:18])[C:11]=3[CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 66830431HCID 66830431, compound

Product 3

HCID 57853806HCID 57853806, compoundHCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideHCID 66830431HCID 66830431, compoundYield 30%

Procedure

2-[5-Chloro-2-(1-methyl-5-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-7-ylamino)-pyrimidin-4-ylamino]-N-methylbenzamide. This compound was prepared according to the procedure for Example 417b. From 7-amino-1-methyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (75 mg, 0.39 mmol) and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methylbenzamide (111 mg, 0.37 mmol) was obtained 48 mg (30%) of the title compound following preparative tlc (20% MeOH/DCM); m.p. 235-245° C. (dec.); MS: m/z/=452/454 (M+H)+, Cl-isotope pattern; 1H-NMR (DMSO-d6, δ): 11.64 (s, 1H), 9.36 (s, 1H), 8.75 (m, 2H), 8.19 (s, 2H), 7.76 (d, 7 Hz, 1H), 7.70 (m, 2H), 7.47 (t, 7 Hz, 1H), 7.11 (t, 7 Hz, 1H), 6.88 (d, 8 Hz, 1H), 3.13 (m, 4H), 2.79 (s, 3H), 2.75 (s, 3H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-fe8c57772b174bc89ccfcd78c4c759c3
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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