2-Bromoethyl methyl ether → HCID 67264437, compound

HRID 1687202Notes

Reaction equation

HRID 1687202 reaction equation
[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[N:4][C:5]([NH:8][C:9]2[CH:24]=[CH:23][C:12]3[N:13]([CH3:22])[CH2:14][CH2:15][N:16]([CH2:18][CH2:19][O:20][CH3:21])[CH2:17][C:11]=3[CH:10]=2)=[N:6][CH:7]=1.ClC1C(NC2C=CC=CC=2NS(C)(=O)=O)=NC(NC2C=CC3N(C)CCNCC=3C=2)=NC=1.C(N(C(C)C)CC)(C)C.BrCCOC>CN(C=O)C>[NH4+:4].[OH-:20].[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH:32][S:33]([CH3:36])(=[O:34])=[O:35])=[N:4][C:5]([NH:8][C:9]2[CH:24]=[CH:23][C:12]3[N:13]([CH3:22])[CH2:14][CH2:15][N:16]([CH2:18][CH2:19][O:20][CH3:21])[CH2:17][C:11]=3[CH:10]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 809722-Bromoethyl methyl etherHCID 81531DiisopropylethylamineHCID 66830684HCID 66830684, compoundHCID 67264437HCID 67264437, compound

Product 2

HCID 14923Ammonium HydroxideHCID 67264437HCID 67264437, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-{5-Chloro-2-[4-(2-methoxy-ethyl)-1-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-7-ylamino]-pyrimidin-4-ylamino}-phenyl)-methanesulfonamide. To a solution of N-{2-[5-chloro-2-(1-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-7-ylamino)-pyrimidin-4-ylamino]-phenyl}-methanesulfonamide (53 mg, 0.11 mmol) in DMF (2 mL) was added diisopropylethylamine (30 μL) and 1-bromo-2-methoxyethane (31 μL, 0.34 mmol). A few milligrams of KI was added and the mixture was allowed to stir at room temperature overnight. Preparative tlc (1% NH4OH/10% MeOH/DCM) afforded 28 mg (47%) of the title compound; m.p. 203-210° C.; MS: m/z=531 (M−H)+; 1H-NMR (CDCl3, δ): 7.98 (s, 1H), 7.83 (m, 1H), 7.36 (d, 6 Hz, 1H), 7.28 (2, 2H), 7.22 (m, 1H), 7.14 (s, 1H), 6.73 (d, 8 Hz, 1H), 3.71 (s, 2H), 3.44 (t, 6 Hz, 2H), 3.30 (s, 3H), 2.94 (m, 6H), 2.88 (s, 3H), 2.83 (s, 3H).

Workup

  1. additionA few milligrams of KI was added

Sources & evidence

ORD record
ord-327800e3b48848d4b3bf8685b062d1bf
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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