Pyrrolidine → HCID 44124482, compound

HRID 2040975Notes

Reaction equation

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

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 57747913HCID 57747913, compound

Product 1

HCID 44124482HCID 44124482, compound

Procedure

The title compound was prepared by the method of Example 34, substituting (R)-1-(6-bromobenzo[d]thiazol-2-yl)piperidin-3-yl methanesulfonate (Reference Example 12) in place of (S)-1-(6-bromobenzo[d]thiazol-2-yl)piperidin-3-yl methanesulfonate (Reference Example 10) and substituting pyrrolidine in place of azetidine to give (S)-6-bromo-2-(3-(pyrrolidin-1-yl)piperidin-1-yl)benzo[d]thiazole. 1H NMR (300 MHz, CD3OD) δ ppm 1.47-1.75 (m, 2H), 1.77-1.95 (m, 5H), 2.11-2.20 (m, 1H), 2.28-2.39 (m, 1H), 2.67-2.76 (m, 4H), 3.06-3.25 (m, 2H), 3.87-3.96 (m, 1H), 4.25-4.32 (m, 1H), 7.33 (d, J=9 Hz, 1H), 7.39 (dd, J=2, 9 Hz, 1H), 7.79 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 366 (M+H)+.

Workup

customThe title compound was prepared by the method of Example 34

Sources & evidence

ORD record: ord-7dde157cf30d460ebe7446af4bf42037
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580968B2

Reaction notes

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