Formic Acid → HCID 71251281, compound

HRID 1055148Notes

Reaction equation

HRID 1055148 reaction equation
[C:1]12([CH:11]([NH:16][C:17]3[C:22]([F:23])=[CH:21][N:20]=[C:19]([C:24]4[C:32]5[C:27](=[N:28][CH:29]=[C:30](F)[CH:31]=5)[NH:26][CH:25]=4)[N:18]=3)[CH2:12][C:13]([OH:15])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Cl:34]C1C=C2C(B3OC(C)(C)C(C)(C)O3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1.FC1C=C2C(B3OC(C)(C)C(C)(C)O3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1.C(O)=O>C(#N)C>[C:1]12([CH:11]([NH:16][C:17]3[C:22]([F:23])=[CH:21][N:20]=[C:19]([C:24]4[C:32]5[C:27](=[N:28][CH:29]=[C:30]([Cl:34])[CH:31]=5)[NH:26][CH:25]=4)[N:18]=3)[CH2:12][C:13]([OH:15])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 284Formic AcidHCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 672856905-fluoro-1-((4-methylphenyl)sulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 71247905HCID 71247905, compound

Product 1

HCID 71251281HCID 71251281, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 94 was synthesized in a manner similar to 3-(1-Adamantyl)-3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]propionic acid, 86, using 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine instead of boronate ester, 7a: 1H NMR (400 MHz, CD3OD) δ 9.02 (d, J=2.3 Hz, 1H), 8.40-8.24 (m, 2H), 8.18 (d, J=5.0 Hz, 1H), 4.91 (d, J=11.6 Hz, 1H), 2.88 (dd, J=16.0, 2.8 Hz, 1H), 2.65 (dd, J=15.9, 11.0 Hz, 1H), 2.01 (s, 3H), 1.77 (dd, J=27.9, 11.9 Hz, 12H); LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=2.60 minutes (M+H) 470.27.

Sources & evidence

ORD record
ord-718108ec9c2c46ffa7bf7baff7a6d494
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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