HCID 86680991, compound → HCID 86681001, compound

HRID 1847965Notes

Reaction equation

HRID 1847965 reaction equation
[N:1]1([CH2:10][C:11]2[CH:20]=[CH:19][C:14]3[N:15]=[C:16]([Br:18])[S:17][C:13]=3[CH:12]=2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2]1.BrC1SC2C=C(CN3C4C=C(OC)C(OC)=CC=4N=C3)C=CC=2N=1>>[N:5]1[C:6]2[C:2]([N:1]([CH2:10][C:11]3[CH:20]=[CH:19][C:14]4[N:15]=[C:16]([Br:18])[S:17][C:13]=4[CH:12]=3)[CH:9]=[CH:8][CH:7]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 86680991HCID 86680991, compoundHCID 86681002HCID 86681002, compound

Product 1

HCID 86681001HCID 86681001, compound

Procedure

(1R,2R)-2-((6-((1H-Imidazo[4,5-b]pyridin-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol (41 mg, 42%) was obtained as a white solid using a procedure analogous to that described in Step 5 of Example 2, substituting the 6-((1H-imidazo[4,5-b]pyridin-1-yl)methyl)-2-bromobenzo[d]thiazole (Isomer 2) from Step 1 of this Example for 2-bromo-6-((5,6-dimethoxy-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazole used in Example 2. 1H NMR (300 MHz, DMSO-d6) δ 8.66 (s, 1H), 8.35-8.44 (m, 1H), 8.00 (d, J=7.0 Hz, 2H), 7.69 (s, 1H), 7.12-7.36 (m, 3H), 5.50 (s, 2H), 4.77 (br s, 1H), 3.24-3.40 (m, 2H), 2.02 (d, J=10.2 Hz, 1H), 1.87 (d, J=9.4 Hz, 1H), 1.62 (d, J=4.9 Hz, 2H), 1.22 (d, J=6.0 Hz, 4H). LCMS (ESI) m/z 380 (M+H)+.

Sources & evidence

ORD record
ord-24af084c1c22467e8f03f7681ae9d6e9
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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