HCID 71549044, compound → HCID 86681095, compound

HRID 1848122Notes

Reaction equation

HRID 1848122 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH2:10][C:11]3[CH:27]=[CH:26][C:14]4[N:15]=[C:16]([NH:18][C@@H:19]5[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]5[OH:25])[S:17][C:13]=4[CH:12]=3)[C:6]=2[CH:28]=1.BrC1C=CC2N(CC3C=CC4N=C(N[C@@H:46]5CCCC[C@H:47]5[OH:52])SC=4C=3)C=NC=2C=1>>[OH:25][C@@H:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C@H:19]1[NH:18][C:16]1[S:17][C:13]2[CH:12]=[C:11]([CH2:10][N:7]3[C:6]4[CH:28]=[C:2]([C:47](=[O:52])[CH3:46])[CH:3]=[CH:4][C:5]=4[N:9]=[CH:8]3)[CH:27]=[CH:26][C:14]=2[N:15]=1

Participants

3

Reactant 2

HCID 71549044HCID 71549044, compoundHCID 71549174HCID 71549174, compound

Product 1

HCID 86681095HCID 86681095, compound

Procedure

1-(1-((2-(((1R,2R)-2-Hydroxycyclohexyl)amino)benzo[d]thiazol-6-yl)methyl)-1H-benzo[d]imidazol-6-yl)ethanone was synthesized as a white powder (8 mg, 6%) using a procedure analogous to that described in Example 110, substituting (1R,2R)-2-((6-((6-bromo-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol from Steo 6 of Example 107 for (1R,2R)-2-((6-((5-bromo-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol used in Example 110. 1H NMR (300 MHz, DMSO-d6) δ 8.60 (s, 1H), 8.24 (s, 1H), 7.99 (d, J=7.5 Hz, 1H), 7.82 (m, 1H), 7.74 (m, 1H), 7.68 (s, 1H), 7.31 (m, 1H), 7.21 (m, 1H), 5.58 (s, 2H), 4.75 (d, J=5.1 Hz, 1H), 3.51 (m, 1H), 3.35 (m, 1H), 2.61 (s, 3H), 2.02 (m, 1H), 1.87 (m, 1H), 1.55-1.67 (m, 2H), 1.10-1.34 (m, 4H); LCMS (ESI) m/z 421 (M+H)+.

Sources & evidence

ORD record
ord-67d94268130143468311b1299a1e8209
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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