Potassium Carbonate → HCID 25159285, compound

HRID 1041799Notes

Reaction equation

HRID 1041799 reaction equation
[Cl:1][C:2]1[C:3]([NH:21][C:22]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([NH:26][CH3:27])=[O:25])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][NH:17][CH2:16][C:15](=[O:19])[NH:14][C:13]=3[CH:20]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:40][CH2:41][C:42]([F:45])([F:44])[F:43]>C(O)CCC>[Cl:1][C:2]1[C:3]([NH:21][C:22]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([NH:26][CH3:27])=[O:25])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][N:17]([CH2:40][CH2:41][C:42]([F:45])([F:44])[F:43])[CH2:16][C:15](=[O:19])[NH:14][C:13]=3[CH:20]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1561651,1,1-Trifluoro-3-iodopropaneHCID 67264717HCID 67264717, compound

Product 1

HCID 25159285HCID 25159285, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2-[5-chloro-2-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-3-fluoro-N-methyl-benzamide (50 mg, 0.11 mmol), potassium carbonate (31 mg, 0.22 mmol) and 1-iodo-3,3,3-trifluoropropane (58 mg, 0.25 mmol) was heated at 115° C. in butanol (3 mL) for 24 hours. After evaporated solvent, chromatography of the crude solid on a TLC plate with methylene chloride and methanol (25:1) to give 15.6 mg of 2-{5-chloro-2-[2-oxo-4-(3,3,3-trifluoro-propyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino]-pyrimidin-4-ylamino}-3-fluoro-N-methyl-benzamide in 14% yield: 1H NMR (300 MHz, CDCl3) δ 8.82 (s, 1H), 8.2 (s, 1H), 7.6 (m, 2H), 7.43 (m, 2H), 7.24 (s, 1H), 7.15 (d, 1H), 6.9 (d, 1H), 6.43 (d, 1H), 3.85 (s, 2H), 3.53 (s, 2H), 3.07 (d, 3H), 2.97 (m, 2H), 2.46 (m, 2H); MS (m/e): 552.2 (M+1).

Workup

  1. customAfter evaporated solvent, chromatography of the crude solid on a TLC plate with methylene chloride and methanol (25:1)

Sources & evidence

ORD record
ord-a5609de08c5b43fd9e07ed583b421f85
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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