(R)-Tert-butyl (4-fluoro-1-hydroxy-4-methylpentan-2-YL)carbamate → 4-fluoro-4-methyl-1-(5-methyl-5H-chromeno[3,4-c]pyridin-8-yloxy)pentan-2-amine

HRID 2369539Notes

Reaction equation

HRID 2369539 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[CH:11][N:12]=[CH:13][CH:14]=3)[CH:9]([CH3:16])[O:8][C:6]=2[CH:7]=1.C(OC(=O)[NH:23][CH:24]([CH2:27][C:28]([F:31])([CH3:30])[CH3:29])[CH2:25][OH:26])(C)(C)C>>[F:31][C:28]([CH3:30])([CH3:29])[CH2:27][CH:24]([NH2:23])[CH2:25][O:26][C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[CH:11][N:12]=[CH:13][CH:14]=3)[CH:9]([CH3:16])[O:8][C:6]=2[CH:7]=1

Participants

3

Reactant 2

HCID 78166485(R)-Tert-butyl (4-fluoro-1-hydroxy-4-methylpentan-2-YL)carbamateHCID 866958958-chloro-5-methyl-5H-chromeno[3,4-c]pyridine

Product 1

HCID 717267684-fluoro-4-methyl-1-(5-methyl-5H-chromeno[3,4-c]pyridin-8-yloxy)pentan-2-amineYield 99%

Procedure

Prepared as described in Example 8, Part D using 8-chloro-5-methyl-5H-chromeno[3,4-c]pyridine (0.100 g, 0.432 mmol) and tert-butyl(4-fluoro-1-hydroxy-4-methylpentan-2-yl)carbamate (0.168 g, 0.712 mmol) to afford 4-fluoro-4-methyl-1-(5-methyl-5H-chromeno[3,4-c]pyridin-8-yloxy)pentan-2-amine (80 mg, 0.23 mmol, 99% yield) as a yellow oil. 1H NMR (400 MHz, MeOD) δ 8.66 (d, J=6.4 Hz, 1 H), 8.64 (s, 1 H), 8.24 (d, J=6.4 Hz, 1 H), 8.08 (d, J=8.8 Hz, 1 H), 6.94 (dd, J=2.4 Hz, 8.8 Hz, 1 H), 6.78 (d, J=2.8 Hz, 1 H), 5.57 (q, J=6.4 Hz, 1 H), 4.38 (dd, J=6.4 Hz, J=10.8 Hz,1 H), 4.22 (dd, J=6.4 Hz, 10.8 Hz, 1 H), 3.99 (m, 1 H), 2.16 (m, 2 H), 1.75 (d, J=6.8 Hz, 3 H), 1.55 (s, 3 H), 1.50 (s, 3 H); LCMS (ESI) m/e 331.2 [(M+H)+, calcd for C19H24FN2O2331.2] LC/MS retention time (method D): tR=0.97 min; HPLC retention time (method B): tR=8.04 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-24e35759208b4b518830a217a4311671
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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