Hydrogen Bromide → HCID 178517614, compound

HRID 1692020Notes

Reaction equation

HRID 1692020 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:28]=[CH:27][C:12]3[N:13]=[C:14]([N:16]4[CH2:20][CH2:19][C@@H:18]([N:21]5[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]5)[CH2:17]4)[S:15][C:11]=3[CH:10]=2)=[CH:5][N:4]=1.Br>>[N:21]1([C@@H:18]2[CH2:19][CH2:20][N:16]([C:14]3[S:15][C:11]4[CH:10]=[C:9]([C:6]5[CH:7]=[N:8][C:3]([OH:2])=[N:4][CH:5]=5)[CH:28]=[CH:27][C:12]=4[N:13]=3)[CH2:17]2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 44124248(R)-6-(2-methoxypyrimidin-5-yl)-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole

Product 1

HCID 178517614HCID 178517614, compound

Procedure

A solution of (R)-6-(2-methoxypyrimidin-5-yl)-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole (Example 15, 20 mg, 0.051 mmol) in hydrobromic acid (48 wt. % in water, 0.25 mL, 2.2 mmol) was heated to 80° C. for 1 hour, concentrated with a stream of nitrogen and chromatographed on silica gel eluting with 2 to 20% (9:1 methanol:ammonium hydroxide) in CH2Cl2 to provide the desired product. 1H NMR (300 MHz, CD3OD) δ ppm 1.48-1.57 (m, 2H), 1.62-1.72 (m, 4H), 1.98-2.10 (m, 1H), 2.32-2.43 (m, 1H), 2.47-2.67 (m, 4H), 3.05-3.19 (m, 1H), 3.39-3.46 (m, 1H), 3.52-3.62 (m, 1H), 3.71-3.80 (m, 1H), 3.84-3.92 (m, 1H), 7.49 (dd, J=8.5, 1.7 Hz, 1H), 7.55 (d, J=8.5 Hz, 1H), 7.90 (d, J=1.4 Hz, 1H), 8.59 (s, 2H); MS (DCI/NH3) m/z 382 (M+H)+.

Workup

  1. concentrationconcentrated with a stream of nitrogen
  2. customchromatographed on silica gel eluting with 2 to 20% (9:1 methanol:ammonium hydroxide) in CH2Cl2

Sources & evidence

ORD record
ord-8c01218c7f9c41929a6b96f680cffac2
Source dataset
uspto-grants-2012_04
Patent number
US08153813B2

Reaction notes

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