Diisopropylethylamine → HCID 71550271, compound

HRID 1848018Notes

Reaction equation

HRID 1848018 reaction equation
[Br:1][C:2]1[C:23]([O:24][CH3:25])=[CH:22][C:5]2[N:6]([CH2:9][C:10]3[CH:21]=[CH:20][C:13]4[N:14]=[C:15](S(C)=O)[S:16][C:12]=4[CH:11]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.[NH2:26][C@@H:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][C@H:28]1[OH:36].CCN(C(C)C)C(C)C>>[Br:1][C:2]1[C:23]([O:24][CH3:25])=[CH:22][C:5]2[N:6]([CH2:9][C:10]3[CH:21]=[CH:20][C:13]4[N:14]=[C:15]([NH:26][C@@H:27]5[C:35]6[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=6)[CH2:29][C@H:28]5[OH:36])[S:16][C:12]=4[CH:11]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 69311541-Amino-2-indanol, trans-(-)-HCID 86681039HCID 86681039, compound

Product 1

HCID 71550271HCID 71550271, compoundYield 20%

Conditions

Temperature
160 °C

Procedure

To a suspension of 6-((5-bromo-6-methoxy-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole (279 mg, 0.07 mmol) and (1R,2R)-1-amino-2,3-dihydro-1H-inden-2-ol (30 mg, 0.2 mmol) was added DIEA (60 μL, 0.3 mmol). The mixture was heated in a Biotage microwave synthesizer at 160° C. in a sealed tube for 30 min. The mixture was then subjected to purification by reverse-phase preparative HPLC using a mixture of water (5% CH3CN, 0.05% HCOOH) and CH3CN (0.05% HCOOH) as the mobile phase and Varian Pursuit XRs C18 column as the stationary phase to afford (1R,2R)-1-((6-((5-bromo-6-methoxy-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)-2,3-dihydro-1H-inden-2-ol (7 mg, 20%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ 8.48 (d, J=7.9 Hz, 1H), 8.31 (s, 1H), 7.86 (s, 1H), 7.72 (s, 1H), 7.33-7.41 (m, 2H), 7.28 (m, 1H), 7.12-7.24 (m, 4H), 5.49 (s, 2H), 5.17 (t, J=7.1 Hz, 1H), 4.29 (br s, 1H), 3.87 (s, 3H), 3.16 (dd, J=7.0, 15.6 Hz, 1H), 2.74 (dd, J=7.3, 15.5 Hz, 1H). LCMS (ESI) m/z 522 and 524 (M+H)+.

Workup

  1. customThe mixture was then subjected to purification by reverse-phase preparative HPLC
  2. additiona mixture of water (5% CH3CN, 0.05% HCOOH) and CH3CN (0.05% HCOOH) as the mobile phase and Varian Pursuit XRs C18 column as the stationary phase

Sources & evidence

ORD record
ord-cc89736d2d1f461aa4eda9691a457cff
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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