(Dimethyl sulfide)trihydroboron → HCID 57955649, compound

HRID 1880985Notes

Reaction equation

[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=O)[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.B.CSC>C1COCC1>[CH:1]1([N:6]2[CH2:12][C:11]([F:13])([F:14])[CH2:10][N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([CH2:26][OH:27])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

The title compound was synthesized by solubilizing 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid (0.36 mmol) in THF (20 mL), and adding borane-dimethylsulfide (2.0M, 1.8 mL, 3.6 mmol) slowly. The solution was stirred for 18 h and then heated to 50° C. for 2 hours. The reaction mixture was then washed with water (×2), brine, and the solvent evaporated. The final compound was purified by reverse phase HPLC and basified to give the free base (8.1 mg, 5% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37-1.96 (m, 8 H) 2.82 (s, 3 H) 3.48 (t, J=13.39 Hz, 2 H) 3.78 (t, J=12.00 Hz, 2 H) 3.86 (s, 3 H) 4.43 (d, 2 H) 4.84 (t, J=7.83 Hz, 1 H) 5.07 (t, J=5.81 Hz, 1 H) 6.82 (d, J=8.34 Hz, 1 H) 6.95 (s, 1 H) 7.31 (s, 1 H) 7.66 (s, 1 H) 8.21 (d, J=8.08 Hz, 1 H). [M+H] calculated for C21H27F2N5O2, 420; found 420.

Workup

washThe reaction mixture was then washed with water (×2), brine
customthe solvent evaporated
customThe final compound was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-4e72590f17bc4ee5bda96b5e53290a1d
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318727B2

Reaction notes

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