Acetone → HCID 57955586, compound

HRID 1880976Notes

Reaction equation

HRID 1880976 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:37])[C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[CH:16][C:17]4[N:23]([CH3:24])[C:22](=[O:25])[C:21]([F:27])([F:26])[CH2:20][N:19]([CH:28]5[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]5)[C:18]=4[N:34]=3)=[C:9]([O:35][CH3:36])[CH:8]=2)[CH2:2]1.CO.[CH3:40][C:41]([CH3:43])=O.N1C=CC=CC=1.B>C(O)(=O)C.ClCCl>[CH:28]1([N:19]2[CH2:20][C:21]([F:27])([F:26])[C:22](=[O:25])[N:23]([CH3:24])[C:17]3[CH:16]=[N:15][C:14]([NH:13][C:10]4[CH:11]=[CH:12][C:7]([C:6]([NH:5][CH:3]5[CH2:4][N:1]([CH:41]([CH3:43])[CH3:40])[CH2:2]5)=[O:37])=[CH:8][C:9]=4[O:35][CH3:36])=[N:34][C:18]2=3)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 2723995Borane;pyridineHCID 25254000HCID 25254000, compound

Product 1

HCID 57955586HCID 57955586, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was synthesized by solubilizing N-(azetidin-3-yl)-4-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzamide (33 mg, 0.07 mmol) in acetic acid: methanol: dichloromethane (1 mL of 1:2:2) and treatment with acetone (58 mg, 1.0 mmol), and borane-pyridine (100 μL, 0.8 mmol). The reaction was left to stir for 3 hours. The reaction solvent was removed and the final compound was purified by reverse phase HPLC and basified to give the free base (5.7 mg, 16% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.87 (d, J=6.06 Hz, 6 H) 1.48-1.78 (m, 8 H) 1.93 (br. s., 2 H) 2.24-2.36 (m, 1 H) 2.94 (t, J=6.82 Hz, 2 H) 3.33 (s, 3 H) 3.51 (t, J=6.82 Hz, 2 H) 3.94 (s, 3 H) 4.05 (t, J=14.02 Hz, 2 H) 4.39 (q, J=6.99 Hz, 1 H) 4.70-4.83 (m, 1 H) 7.49 (d, 0 H) 7.51 (s, 1 H) 7.98 (s, 1 H) 8.26 (s, 1 H) 8.29 (d, 1 H) 8.61 (d, J=6.82 Hz, 1 H). [M+H] calculated for C28H37F2N7O3, 574; found 574.

Workup

  1. waitThe reaction was left
  2. customThe reaction solvent was removed
  3. customthe final compound was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-284d0b3a00d543c9a3473749afdff298
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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