Bromotrimethylsilane → HCID 11525606, compound

HRID 229462Notes

Reaction equation

[P:1]([O:33]C)([O:31]C)([O:3][C:4]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[N:10]([CH2:19][C:20]([N:22]([CH2:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH3:24])=[O:21])[N:9]=1)=[C:5]([CH3:7])[CH3:6])=[O:2].C[Si](Br)(C)C>>[P:1]([OH:31])([OH:33])([O:3][C:4]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[N:10]([CH2:19][C:20]([N:22]([CH2:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH3:24])=[O:21])[N:9]=1)=[C:5]([CH3:6])[CH3:7])=[O:2]

Participants

Reactant 2

HCID 76113Bromotrimethylsilane

HCID 68851856HCID 68851856, compound

Product 1

HCID 11525606HCID 11525606, compound

Procedure

Reaction of 1-(1-{2-[(3,3-dimethylbutyl)(ethyl)amino]-2-oxoethyl}-6-methoxy-1H-indazol-3-yl)-2-methylprop-1-en-1-yl dimethyl phosphate with trimethylsilyl bromide as described in Example 2 provided the title compound. It was isolated by RP-HPLC using 10-100% MeCN gradient without TFA as a colorless solid following lyophilization. 1H NMR (CD3CN, 500 MHz) showed two amide rotomers in about 6:7 ratio: δ 7.55 (d, 8.7 Hz, 1H), 6.88 & 6.87 (d, 1.9 Hz, 1H), 6.84 (dd, 2.1 & 8.9 Hz, 1H), 5.23 & 5.21 (s, 2H), 3.88 & 3.87 (s, 3H), 3.31˜3.48 (m, 4H, overlapping with residual water peak), 1.94 (d, 1.8 Hz, 3H), 1.81-1.82 (m, 3H), 1.61-1.64 & 1.42˜1.46 (m, 2H), 1.26 & 1.10 (t, 7.1 Hz, 3H), 0.99 & 0.91 (s, 9H). LC-MS: 3.18 min. (m/Z=370.2, 468.1).

Sources & evidence

ORD record: ord-8a8d1cc229b74696a7cfb79d9655ae04
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563816B2

Reaction notes

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